WINCHESTER NEWS A TRUSTED AND RELIABLE SOURCE OF LOCAL NEWS
2026 Spring Town Meeting wraps
Session 4 · Thursday, May 7 · 7 p.m. · Winchester High School Auditorium, 80 Skillings Road
BY WILL DOWD

Live from the floor

Follow the feed for updates as votes happen, then scroll to the tracker for the status of all 46 articles.

Support the reporting behind this tracker. Winchester News is free, independent and powered entirely by readers. Make a donation to keep local journalism going.
Live updates · Session 4 · Thursday, May 7 Jump to article tracker ↓
Session 4 · Thursday, May 7
Town Meeting adjourns and dissolves; carriage house study committee indefinitely postponed
The 2026 Spring Annual Town Meeting adjourned and dissolved Thursday night after indefinitely postponing the only motion filed under Article 46, the closing-business article: a Select Board and School Committee proposal to authorize a new study committee on the future of the Sanborn carriage house at 21 High Street, the Ambrose Elementary outbuilding whose $300,000 demolition was rejected last week under Article 25.

Select Board Chair Anthea Brady of Precinct 1 presented the proposal alongside School Committee Chair Tim Matthews of Precinct 1. The five-member committee — one appointee each from the Select Board, School Committee, Capital Planning Committee, Finance Committee and Historical Commission — would meet with the Winchester Historical Society and report back to fall and spring 2027 Town Meetings. By two weeks before the fall warrant closes, the Historical Society would have to demonstrate “tangible progress” toward a public-private partnership: a project narrative and conceptual drawings of all sides of the building, a preliminary private budget, an opinion from a licensed structural engineer that the building is sound, and a financial commitment showing private fundraising progress. By spring 2027, the bar would rise to interior blueprints, exterior renderings, abatement plans for mold and asbestos, traffic and pedestrian safety analysis, and demonstrated financial progress. Brady noted the article had been amended on the floor to bar Society board members and their immediate family from the study committee.

Bill Swanton of Precinct 5, who serves on the Historical Society board, opposed the article, calling the benchmarks “very aggressive” given Community Preservation Act and other funding cycles. “A hair trigger that says, well, if you don’t get all this done, we’re just going to tear down the building, is not in the spirit of what was voted the other night,” he said.

Doug Marmon of Precinct 1 moved to postpone the article to fall Town Meeting to allow more negotiation time. Moderator Phil Frattaroli ruled that motion out of order: Town Meeting cannot place items on a future warrant; the Select Board has the authority to create such a committee on its own. Frattaroli said an indefinite-postponement motion would, however, be in order.

Norah Cooney of Precinct 5, whose backyard abuts the carriage house, supported keeping the benchmarks. She said vandalism, drug paraphernalia and recent break-in attempts make the building a real safety concern, and that securing the property in the meantime will carry costs the town will need to absorb if private fundraising stalls. She said she has already begun corresponding with police and fire commissioners about securing the building.

Christian Nixon of Precinct 1 walked Town Meeting through the actual cost picture. The $7 million figure rejected by Town Meeting in 2022, he said, was for a full envelope rebuild that included demolition of the 1960s concrete-block wing and an elevator (now closer to $1 million on its own); piecemeal estimates from two to three years ago put the roof and envelope at $1 million to $1.5 million and interior abatement at $500,000 to $1 million. Nixon then moved to indefinitely postpone Article 46.

Stefanie Mnayarji of Precinct 5, who had presented Article 25, urged action: increasing vandalism, fresh graffiti and Halloween-night parent patrols outside the building have made it a growing liability. Pamela Cort of Precinct 5 drew the procedural line that decided the vote: the Select Board has the authority to create exactly this committee on its own, with the same goals, without a Town Meeting vote.

Town Meeting moved the question and then voted to indefinitely postpone Article 46. Frattaroli closed: “That brings us to the end of our warrant.” A motion to adjourn and dissolve carried, ending the 2026 Spring Annual Town Meeting after four sessions.
Article 45 passes amended — EFPBC adds two seats after the night’s longest debate
Article 45, an amendment to the membership of the Educational Facilities Planning and Building Committee — the body that oversees school facility design and construction, including the upcoming Muraco rebuild — has become the longest debate of the night, eclipsing both the FY27 budget debate and Article 42’s ranked-choice voting discussion. The article would add one sentence to the EFPBC’s constituting language: the member appointed by the School Committee serves at the School Committee’s pleasure.

Select Board member Bill McGonigle of Precinct 3 presented for the board. He told members the EFPBC’s constituting language is itself scattered across “seven or eight different motions from town meeting over the last 20-something years” rather than collected in a single bylaw. The amendment, he said, lets the School Committee seat one of its own members during periods when MSBA compliance or active project work demands it — and substitute a non-member during quieter times. McGonigle tied the change to the Muraco rebuild. “If you support Muraco, you probably want to have somebody on the school committee, on the EFPBC, so that feasibility study can go forward,” he said.

School Committee Chair Tim Matthews of Precinct 1 said the committee voted 5-0 favorable. Under MSBA rules a body designated as a School Building Committee must include a sitting School Committee member, he said, and the EFPBC currently does not. Town Meeting has already authorized the EFPBC to spend the $1.5 million Muraco feasibility-study appropriation passed last week, but the committee “can’t currently qualify under MSBA regulations to be a school building committee.”

Then EFPBC Vice Chair Christian Nixon of Precinct 1, who holds the EFPBC seat that earlier drafts of the article would have eliminated, rose to deliver the EFPBC’s recommendation. “This is not awkward, is it?” he opened. The revised motion now before Town Meeting addresses one of the EFPBC’s concerns — an earlier draft would have removed three members, including a Moderator appointment and a member from the Disability Access Commission — but the committee’s core objections remain. The EFPBC voted unanimously to recommend unfavorable action.

Nixon said the “serves at the pleasure of” structure would have a single appointee “essentially performing for an audience of one, or in this case, three, since three constitutes a quorum of the school committee.” He said the gestation period for school building projects is years, not months, that institutional knowledge accumulates over time, and that the change could be precedent-setting for other public bodies. He flagged the proposed July 1 effective date as “a very difficult time for a change” given active concrete-repair work at the high school he is personally helping oversee.

Nixon disputed a factual claim from an April memo Select Board member Paras Bhayani of Precinct 8 circulated, which had argued the EFPBC has no School Committee member and is therefore out of MSBA compliance. Nixon said other Massachusetts municipalities with standing building committees commonly amend their existing committee for an MSBA project rather than restructuring its underlying membership, and noted that the background section in members’ motion books has since been corrected. He told members the EFPBC’s master-planning consultant SMMA was “eager to begin” short- and long-term facility work in February, but the EFPBC asked SMMA to wait first because of collective-bargaining work, then because of the override campaign, and most recently until after this Town Meeting.

Bhayani took the microphone to defend the memo. He said preliminary policy memos at the Select Board are revised and refined as the policy process advances. “If every preliminary memo I wrote got every piece of analysis right from the very start, you should elect me mayor of Winchester,” he said. The original conceptual statement was clarified through staff and town clerk research before the final article was filed.

Megan Blackwell of Precinct 7 asked how Winchester had been MSBA-compliant in the past and whether passing the article would in fact restore compliance. McGonigle said historical compliance was achieved when a sitting School Committee member happened also to be on the EFPBC, and that the gap appeared because the two bodies’ term cycles do not align.

Kathleen Bodie of Precinct 3 drew the discussion onto a wider point. Citing 963 CMR 2.06, she said an MSBA School Building Committee requires not just a school-committee member but also the local CEO or administrator, the person responsible for school-building maintenance, the school principal, a local budget officer, two engineering- or construction-experienced members, and a procurement-certified member. McGonigle acknowledged the article addresses only one of those deficiencies and said additional work may be needed.

Town Counsel, called to clarify, told the meeting that under 963 CMR 2.06 and Massachusetts General Laws Chapter 71, Section 68, a School Committee member is in fact required to be part of the school building committee.

Diab Jerius of Precinct 8 opposed the article. He said the situation is an aberration that will largely correct itself in 10 months when the relevant terms expire, and that allowing one body to remove an appointee mid-term sets a precedent that could undermine volunteers across town. “A lot of boards appoint people to other boards. ... I really don’t think it’s appropriate for a board to all of a sudden say, hey, we don’t think you’re good enough anymore,” he said.

Kara Nierenberg of Precinct 7, who joined the EFPBC last summer as a jointly appointed engineer member, called the proposal “almost insulting” to volunteer board members. She said it took her 10 months of weekly meetings to fully come up to speed on the EFPBC’s technical work, and that being subject to mid-term removal would be discouraging. She said the article also “feels somewhat targeted” toward Nixon and that the EFPBC was not consulted in advance — the first time she saw the article was in the warrant book.

John Bellaire of Precinct 2, presenting from the School Committee perspective, told members the MSBA Module 1 eligibility period had a May 1 deadline for designating a school building committee, and that Winchester has already had to ask MSBA for an extension to get into compliance. “This is, simply put, like we’re just trying to be in compliance with the MSBA,” he said. He praised Nixon’s expertise and said he hopes Nixon can continue serving in another capacity.

Brian Vernaglia of Precinct 4, the Planning Board’s clerk speaking for himself, called the conversation “super awkward” but pointed to precedent: as a Planning Board appointee to the Capital Planning Committee and the Permanent Street Tree Committee, he himself serves at the Planning Board’s pleasure. He asked whether failing the article would put the Muraco feasibility study at risk.

Matthews answered that Winchester’s permanent EFPBC, in place since the late 1980s, is unusual statewide; most municipalities form one-off building committees per project. The appointment language was never modernized to match how the School Committee fills seats on other Town Meeting committees, where the standard formula is “from and by” the body. “It’s a notable divergence in practice from how we appoint our school committee members to every other committee in town,” Matthews said.

Late in the debate, former Town Moderator Heather von Mering of Precinct 8 moved a floor amendment that reframed the article: rather than letting the School Committee swap its existing EFPBC member in and out, the EFPBC would simply add two new seats — a sitting School Committee member and the school district’s director of finance. Both McGonigle (Select Board favorable) and Matthews (School Committee 5-0 favorable) backed the amendment. Terence Tirella of Precinct 2, also a current EFPBC member, supported it from the floor; Nixon said he welcomed the amendment, noting that the school district’s finance director Andrew Marin already attends every weekly EFPBC meeting in practice. The amendment carried on a voice vote, and the article passed as amended. The EFPBC now has two new permanent members and Nixon retains his seat.
Article 44 indefinitely postponed — Planning Board hearing not yet held
Town Meeting indefinitely postponed Article 44 by voice vote without debate. The article, brought by Select Board member Mike Bettencourt of Precinct 6, would have amended Section 7.3.19 of the Zoning Bylaw on inclusionary zoning. Moderator Phil Frattaroli explained that under Chapter 40A of the Massachusetts General Laws, a zoning bylaw amendment must first be the subject of a Planning Board public hearing before Town Meeting can act on it. That hearing has not yet taken place. As a result, the only motions in order on Article 44 were a negative motion such as indefinite postponement or a procedural motion such as referral. The chair moved for indefinite postponement, and Town Meeting agreed.
Article 43 ruled out of order; Town Meeting cannot mandate operational actions
Moderator Phil Frattaroli ruled the citizen petition under Article 43 out of order and no vote was taken. The petition, brought by Wyatt Biel of 176 Dothan Street, asked Town Meeting to direct the town manager and DPW to remove an 18-inch municipal stormwater drain pipe installed across his property in 2018 under a temporary easement that expired the same year, and to reroute the runoff through a public right-of-way.

Frattaroli walked Town Meeting through the limit of its own authority. “We can appropriate money, we can create bylaws, we can create study committees, but we can’t mandate an action of the town government,” he said. The petition’s direction to the town manager and DPW was, in his ruling, outside that scope.

He also explained why the article could not be amended to fix the problem on the floor. Citizen petitions are unique, he said: they are signed by 10 community members and submitted by a deadline, “a coalition exists [and] it’s not shot in time,” meaning the article’s text is locked once the petition is filed. “If a citizens petition is poorly constructed, [it’s] difficult to be able to fix it,” he said, adding that Biel is welcome to submit a properly framed petition to a future Town Meeting.
Ranked-choice voting study committee fails by three votes, 72-75
Citizen petitioner John Healey presents Article 42 at the Town Meeting podium
Citizen petitioner John Healey presents Article 42, the proposed ranked-choice voting study committee, from the Town Meeting podium. Winchester News staff photo / Will Dowd
A citizen petition asking Town Meeting to create a study committee on ranked-choice voting narrowly failed Thursday night after a floor debate that, by several members’ reckoning, rivaled or exceeded the time Town Meeting spent earlier in the evening on the FY27 General Fund operating budget. Article 42 failed 72-75, with two abstentions — one of the closest votes of the night and the only one to send Town Meeting members briefly silent as the precinct-by-precinct tally appeared on the projection screen at the front of the auditorium.

The article would not have changed how Winchester votes. It would have established a seven-member committee — the Town Clerk or designee, one member of the Board of Registrars of Voters, three Select Board appointees, one Town Meeting Member appointed by the Moderator and one member designated by the League of Women Voters of Winchester — to study whether to adopt ranked-choice voting for municipal elections and to report back to fall 2026 Town Meeting. Citizen petitioner John Healey, who is not a Town Meeting member and was given the floor by unanimous consent, opened by stressing that point. “Tonight, you’re not voting on any change to the voting system,” he said. “You’re authorizing a committee to study the potential benefits.”

The case from the proponent. Healey framed the proposal around two problems he said exist in plurality voting even at the local level: vote splitting that creates “spoiler” outcomes, and the chilling effect on prospective candidates who decide not to run rather than divide a base of support. He cited Ralph Nader’s 2000 presidential effect in Florida and the 2020 Fourth Congressional District Democratic primary that Jake Auchincloss won with 22 percent of the vote. He named Cambridge and Easthampton as the only Massachusetts municipalities currently using a ranked ballot in their elections, said 10 others have approved adoption and filed home-rule petitions to implement it, and added that Manchester-by-the-Sea has approved its own study committee. He pointed to a 2024 analysis in the journal Electoral Studies that found “the predicted probability of voting in local elections is 17 percent higher in ranked choice jurisdictions than non rank choice jurisdictions, all else being equal.”

Cambridge has used ranked-choice voting in some form for City Council and School Committee elections continuously since 1941, making it the longest-running ranked-ballot system in the United States. Maine and Alaska now use ranked-choice voting for statewide elections, joining a growing list of municipalities, including Portland, Oregon, that have adopted the system in recent years.

Where the boards landed. Select Board Chair Anthea Brady of Precinct 1 said the board took no position on Article 42 because the full proposal had not reached them in time for a formal vote, not because they did not believe the topic was worth studying. There was no Committee on Government Regulations recommendation; Article 42 is not a proposed bylaw, so it falls outside the committee’s charge.

The supporters. Susan Verdicchio of Precinct 1, a member of the steering committee of the Winchester League of Women Voters, urged passage. She tied the article to the league’s long-running commitment to active civic participation, and described comments she said the league has heard during its annual high-school voter-registration drives over the past two or three years. “Why would I vote? I don’t have any politicians I want to vote for. It’s all about money,” she said, paraphrasing students. She added that local-election turnout in Winchester drops noticeably in years without an override or debt-exclusion question.

School Committee Chair Tim Matthews spoke not on behalf of any board he sits on but as a Town Meeting member. He said he grew up in a parliamentary democracy outside the United States and finds the question worth examining, particularly for the relatively rare town-wide races with three or four candidates competing for two seats. “The conclusion very well may be that it’s not beneficial,” he said. “I think that if we were to vote yes, I hope that we would put together a fairly open committee to do so. ... Maybe it’s worth taking a look into and we say no at the end of that — that might be a good outcome for the process.” He added he typically votes against motions to move the vote because “I just like to hear all the perspectives.”

The opposition. John B. Miller of Precinct 6 said he supports studying things in general but worried the article’s charge tilts the committee toward “potential benefits” rather than benefits and harms, and noted that local elections in Winchester are nonpartisan, unlike the national contests Healey used as examples. Monica Ross of Precinct 6 reminded the meeting that Massachusetts voters rejected statewide ranked-choice voting in 2020 by a 55-45 margin, with 80 percent of cities and towns voting against it. She questioned the burden a switch would place on the Town Clerk’s office — new software, training, voter education and more complicated recounts — and said the cost is hard to justify given the night’s budget pressures. “Our system already works well,” she said.

Marilyn A. Gagalis of Precinct 1, who said she worked in Cambridge her entire career, opposed on the grounds that ranked-choice voting there produces “slate politics,” with alliances forming joint tickets that move voters in lockstep across multiple offices. “People are all thinking the same. They all have the same political views. They all have the same routes on the city and how it is run,” she said. “If you want to do a study, that’s great, but make sure you study Cambridge.” Healey responded from the proponent microphone that slate politics also exists in non-ranked-choice cities such as Medford and Lowell, and that there is no evidence ranked-choice voting causes the phenomenon.

Town Meeting member Joshua Bers of Precinct 7 asked whether the proposal could extend to state or presidential elections. Town Clerk Mary Ellen Marshall took the microphone to clarify that Article 42 covers local elections only, and that any change to state or federal contests would require state legislative action. She said Winchester “tends to have what we refer to as under-endorsed elections” — cycles in which a single candidate runs for an open three-year seat — and that, in her professional view, “ranked choice voting I don’t think would work in community of this size.”

Jonathan Cacciola of Precinct 6, a former Cambridge resident, said he sees the case for ranked-choice voting at the state and federal level — he cited California voters in the 2020 Democratic primary — but is “deeply skeptical” on the municipal level. “You’re going to have, like, the Winchester Resident Alliance versus the Winchester Coalition, and that’s how Cambridge works,” he said, warning of “hyper-local partisanship.” The current system, he said, lets him agree with a Select Board member on one issue and disagree on the next without becoming permanent political opponents. A Precinct 4 member followed, calling Article 42 “a solution looking for a problem,” and pointing to the visible diversity of the current Select Board and School Committee as evidence the existing system is already producing varied perspectives.

The Article 42 vote board: Yes 72, No 75, Abstain 2
The electronic vote board at the close of Article 42: Yes 72, No 75, Abstain 2. Winchester News staff photo / Will Dowd
Before the vote, Moderator Phil Frattaroli asked members to turn off phones and other devices, hoping to speed up the electronic system’s tally and get a cleaner read. The board returned 72 yes, 75 no, two abstentions. Article 42 failed; a simple majority was required.
Article 38 passes unanimously — $3.7 million reach into reserves to soften the FY27 tax levy
Town Meeting passed Article 38 unanimously on a voice vote, transferring $3,264,397 from free cash and $450,000 from overlay surplus to reduce the FY27 tax levy. Moderator Phil Frattaroli described the article as a procedural motion that traditionally follows the budget discussion at Winchester Town Meeting, and there was no presentation. Select Board Chair Anthea Brady of Precinct 1 recommended favorable based on an informal poll of board members rather than a formal vote; the Finance Committee also supported the article. The $3.7 million combined draw is the post-override cushion the town is using to limit what taxpayers will be asked to cover through the levy in the year ahead.
Town Meeting takes a quick break, then jumps ahead to Article 38
With the operating budgets and the Personnel Board package adopted, Town Meeting is taking a brief recess before jumping ahead to Article 38, the use of free cash and overlay surplus to reduce the FY27 tax levy. Article 38 was set as the fourth order of business Thursday and was held until the budget articles cleared. The revised motion before members would transfer $3,264,397 from free cash and $450,000 from overlay surplus to lower the tax levy.
Article 33 passes — town wages and firefighter contract funded
After Personnel Board Chair Peter Cheimets’ presentation, Town Meeting moved straight into voting on the six motions under Article 33 with no floor debate. All six motions passed: the 2.5 percent non-union COLA and its $287,540 funding, the three motions implementing the new firefighter contract for FY26 through FY28 and the $373,988 placeholder appropriation for the still-unsettled police contracts.
Up next: Article 33 — the once-a-year vote on town wages and union contracts
Personnel Board Chair Peter Cheimets presents Article 33 to Town Meeting
Personnel Board Chair Peter Cheimets presents Article 33 from the auditorium-floor microphone. Winchester News staff photo / Will Dowd
Town Meeting has moved to Article 33, the Personnel Board’s annual package on town wages. Personnel Board Chair Peter Cheimets is presiding over the presentation now.

Here is what the article actually does. Article 33 is the only point in the year when Town Meeting votes on raises for town employees and on funding the contracts the town has reached with its public-safety unions. Instead of asking members to approve all of it as a single up-or-down question, the Personnel Board breaks it into six separate motions that Town Meeting works through one at a time.

Each motion is voted separately. The package breaks down like this:
# What it does Amount Funding source
1 Amend FY27 non-union pay schedules to add a 2.5 percent COLA effective July 1, 2026 (Schedules 2, 3, 4, 5 and 6). No appropriation
2 Fund the 2.5 percent non-union COLA across town departments (Town Hall, Library, DPW, Council on Aging, Veterans’ Services and others). $287,540 $249,440 tax levy / $10,600 Water and Sewer retained earnings / $27,500 Recreation retained earnings
3 Amend Schedule 10 (Firefighters) per the IAFF Local 1564 MOU dated January 15, 2026: 2.5 percent in FY26, 2.75 percent in FY27 and 2.75 percent in FY28. No appropriation
4 Fund the FY26 firefighter wage adjustments under the new contract. $289,950 Transfer from FY25 Unallocated Wage account
5 Fund the FY27 firefighter wage adjustments under the new contract. $437,572 Tax levy (FY27 Fire Department personnel budget)
6 Set aside money in an “unallocated wage account” for the still-unsettled Police Patrol and Police Superior contracts. Funds released at a later Town Meeting once contracts are signed. $373,988 Tax levy (FY27 Unallocated Wage Account)
Updates to follow as members work through the package.
Articles 29, 30 and 31 pass: General Fund, Water and Sewer and Recreation budgets all clear
After about a dozen motions ticked off in sequence, Town Meeting passed Article 29, the FY27 General Fund operating budget. Members then moved through Article 30, the FY27 Water and Sewer enterprise-fund operating budget — supported by user-rate revenue, including the 7 percent rate increase Town Meeting approved under Article 8 on the opening night — and Article 31, the FY27 Recreation enterprise-fund operating budget, both presented by the Finance Committee. Both passed.

With the three operating budgets adopted, Town Meeting moves on to the remaining FY27 money articles, beginning with Article 32, the revolving-fund spending caps.
Debate closed by motion; Town Meeting now voting Article 29 motion by motion
A Town Meeting member moved the question on Article 29 and the motion to close debate carried, ending discussion on the FY27 General Fund operating budget. Town Meeting is now ticking off the several motions filed under Article 29, voting them in sequence. Updates with totals to follow.
Floor debate on Article 29: math curriculum, enrollment forecasts and a student takes the mic
Lilly Ryan, a Winchester student, addresses Town Meeting on the FY27 budget
Lilly Ryan, a Winchester student, addresses Town Meeting after members granted unanimous consent for her to speak. Winchester News staff photo / Will Dowd
After Select Board Chair Anthea Brady of Precinct 1 and School Committee Chair Tim Matthews of Precinct 1 delivered their recommendations, Town Meeting moved into open floor debate on Article 29.

Norah Cooney, Precinct 5, said she would vote yes but wanted to be clear about what the budget does not do. “We are simply not sufficiently funding our schools,” she said, even before the cuts that come with this budget. She recalled being “shocked” at a School Committee meeting when Superintendent Frank Hackett said he had never worked in a district that did not have math specialists at the elementary level. Winchester finally added them last year, she said, and they have now been let go. Cooney said the district is also losing ESPs and building aides — the staff who help an upset student stay regulated so a class can keep going. “If we do not have an override by the next budget cycle, the cuts are going to be extreme and very real for our kids,” she said.

Select Board member Paras Bhayani of Precinct 8 echoed both Matthews and Ross, saying their messages were “almost entirely consistent.” He said the structural budget gap remains and broke out the 32.5 school-side FTE reductions: about 10 are enrollment-related, 22.5 are not. He noted the literacy specialists Town Meeting added last year are now being laid off, alongside Fire Department and DPW maintenance reductions on the municipal side. “We can’t cut our way out of this. We’re burning cash,” Bhayani said. “The cuts from here would be catastrophic. You really need revenue.” He said Winchester is “at the precipice” of installing a real long-term financial planning process: a multi-year plan with a one-to-three-to-five-year outlook; a common framework with shared assumptions about what rate schools and the municipal side can grow; and a recurring tri-board meeting through the spring. He singled out Finance Committee Chair Derek Ross for thanks — “If anyone sees him this spring or summer, please buy him” a drink, he suggested.

Christina Marshall, Precinct 7, called the agreement “the best result of a bad situation.” She listed concrete consequences: increased class sizes, teacher layoffs, the loss of math specialists, higher athletic fees, lost opportunities to expand high-school electives or add tier-two supports. “These are not hypothetical ramifications. They are our reality,” she said.

Roger Wilson, Precinct 1, defended Proposition 2 1/2. “We don’t have a revenue problem. We can raise revenue at will, at the will of the people,” he said, arguing that override success depends on giving voters confidence they are getting good value — and that the disciplined choices forced by the cap are part of how that trust is built. He then asked Hackett about the enrollment projections that drive much of the school budget, citing past errors at McCall and signs of in-migration in younger grades.

Superintendent Frank Hackett answers questions on Article 29 from the auditorium podium
Superintendent Frank Hackett answers questions about the FY27 school budget from the auditorium-floor microphone. Winchester News staff photo / Will Dowd
Hackett told Wilson the projections are projections. “A lot of assumptions go into those that may or may not come to pass,” he said, citing housing development, immigration and birth rates. “Where we are right now is we are stabilizing our enrollment,” he said, adding that he expects manageable growth spread across K-12 rather than another spike like the one that strained the district years ago.

Joshua Bers of Precinct 7, thanked the boards for the tri-board meetings, calling this the first Town Meeting in his three years where there has not been “direct opposition” among Finance Committee, School Committee and Select Board. He pressed for two changes: more granular school-budget transparency — “every line item” the way some Vermont towns publish — and a longer runway for any future override, citing a less-than-a-month window between Select Board alignment and the failed override vote. (Moderator Phil Frattaroli noted that under Massachusetts law, Town Meeting allocates a single bottom-line amount to the school budget and cannot specify how it is spent; Beers responded that a retrospective line-item report would still help.)

Catherine Mostow, Precinct 8, picked up Cooney’s thread on the math curriculum. She drew the parallel to the Boston Globe report on Winchester literacy, the moment many town residents said they were “shocked” at how the district had fallen behind, and asked Hackett what can be done to avoid the same shock with math.

Hackett said the district’s entire annual curriculum budget has been about $11,000 — “not going to really do much for us” against a need that mirrors the literacy gap. He said the district has begun mapping common math programs already in use and has “great people in place,” but cautioned that next year’s rollout of the Arts and Letters literacy curriculum will already stretch teachers. “You can’t burn people out. They can only do so much,” he said. He told Town Meeting he hopes to come back through next year’s budget process with “solid recommendations about some short-term steps” on math.

Town Meeting then granted unanimous consent for Lilly Ryan, a Winchester student, to address members. Ryan, speaking from the upper-tier microphone, said adults in the room may not fully grasp how acute the situation is for students. She said her brother is in special education and is not currently getting the services he needs to thrive, and that the cuts will make that worse. She cited a survey she helped run that drew more than 90 student responses, with facilities rated 2.1 out of 5 and more than half of respondents saying their buses are overcrowded and class sizes too large.

Ryan said overrides alone are not a sustainable answer. The town needs a broader tax base, she said, including more retail development — even if that means putting up with the lights and noise that come with it. “These inconveniences might annoy you,” she said, “but they’re not worth losing someone’s life over,” describing students losing opportunities and teachers losing jobs.

Debate continued as additional members rose to speak. Town Meeting has not yet voted on Article 29.
Select Board and School Committee back the budget: a ‘bridge budget,’ not a fix
School Committee Chair Tim Matthews speaks to Town Meeting on Article 29
School Committee Chair Tim Matthews addresses Town Meeting on Article 29 on Thursday. Winchester News staff photo / Will Dowd
Following Finance Committee Chair Derek Ross of Precinct 6, Select Board Chair Anthea Brady of Precinct 1 delivered the Select Board’s unanimous favorable recommendation on Article 29 and described the closer working relationship the board, the Finance Committee and the School Committee built over the budget cycle, including tri-board meetings on two nights as Town Meeting approached. She said the boards intend to keep meeting that way through the year so the “momentum doesn’t go away.”

Brady was direct about what the budget does and does not do. “This budget only staunches the bleeding,” she said, echoing Ross’ line that the town is not going to cut its way out of the problem. The reductions, she said, are not just dollars. “We have town employees who will lose their jobs, students who will lose the trusted aides who they thrive under, or the support of adults who they made a connection with in the classroom, access to building support like math specialists and the benefits of smaller classes.”

She rejected the framing that the cuts reflect mismanagement. “This is not a result of poor fiscal management by the town, or suddenly excellent fiscal management when put under a microscope,” she said. The pressures are structural, she said — Proposition 2 1/2, healthcare cost growth, inflation, the consumer price index, tariffs — and shared across Massachusetts, with 45 communities holding override votes for FY26 or FY27 budgets. If Winchester continues to fall short on operating-side overrides, Brady said, the consequences will reach further into the schools, municipal offices, facilities, roads and sidewalks. The Select Board, she said, voted unanimously in favor “because this is the best possible outcome for our town.”

School Committee Chair Tim Matthews of Precinct 1 followed, thanking his colleagues by name — Karen, Tom, Stephanie and John — along with Superintendent Frank Hackett and Andrew Marin for their partnership through what he called an “extraordinarily challenging period.” Matthews said the committee had hoped to give a different speech this spring after a year of analysis and a March override vote, but the override fell short and that outcome carries the consequences Ross described.

He framed the FY27 budget plainly: “We should not pretend this is anything other than a bridge budget for one year only.” The 32 full-time-equivalent reductions, he said, are not abstract numbers but educators, ESPs, interventionists and specialists. “Students may lose trusted educators, ESPs, interventionists and specialists, all adults who help them feel safe, connected and successful in school each day,” he said, adding that families will see reduced supports and fewer opportunities, staff will carry heavier burdens and extracurricular fees will rise.

Matthews echoed Brady on the structural diagnosis. “None of this is the result of poor stewardship by the town or by the Winchester public schools,” he said. “What we are experiencing is the collision between rising costs and an increasingly expensive municipal funding structure that has become unsustainable for communities across Massachusetts.”

He outlined three commitments going forward: approach the reductions with transparency, seriousness and empathy; protect core educational experiences to the greatest extent possible, with the guiding principle of minimizing harm to students’ learning, growth and well-being; and refuse to let financial strain narrow the district’s sense of who belongs.

On that last point, Matthews noted what he believes is a first. “I am honored to serve as what I believe to be the first openly LGBTQ-plus chair of the committee, following Karen Bockwoll and Suh’s service as Winchester’s first Asian-American chair,” he said. He pointed to a vice chair who is the bilingual child of immigrants and a Title I public-school graduate, a colleague from a working-class public-service family, and a newest member who may be the youngest ever elected to the committee. Those milestones matter, he said, “because they shape how we lead and the budget decisions we make.”

Speaking to teachers, Matthews said, “You are the heart of this district, and will remain that way.” Closing, he said the conversation about Winchester’s long-term financial path cannot end with this budget: if the town does not find sustainable paths forward, the pressures will extend beyond the schools into all facets of town life. The School Committee voted 5-0 in favor of the budget. He asked Town Meeting to do the same.
FinCom chair walks Town Meeting through the post-override budget: ‘They are not wrong’
Finance Committee Chair Derek Ross presenting the FY27 budget to Town Meeting
Finance Committee Chair Derek Ross presents the FY27 General Fund operating budget on the floor of Town Meeting on Thursday. Winchester News staff photo / Will Dowd
Opening debate on Article 29, the FY27 General Fund operating budget, Finance Committee Chair Derek Ross of Precinct 6 delivered a roughly 15-minute presentation walking members through what he called the town’s fiscal vital signs — the post-override budget, how the gap was closed and what he believes Winchester still has to fix. As of this update, Town Meeting has not yet voted on the article; debate continues on the floor.

Ross opened by saying this was his last active tour of duty as chair. He said the committee set three goals for the FY27 process: build one budget rather than two parallel versions, have everyone contribute and take ownership, and restore a productive working relationship with the Schools after a difficult exit from the 2025 Spring Town Meeting. “We do have differences sometimes, and we had hard discussions, but I feel like we’d gotten to the point where we kind of lost some trust and communication, and I really made a concerted effort to break that cycle,” he said.

He said the gap going into the year was about $10 million: a $5.1 million deficit identified in Town Manager Chris Senior’s February financial plan, an additional $1.7 million in non-underpinned expenses and roughly $3.1 million in school wage-bill reductions needed to bring the proposed school budget back to a 5 percent increase. The 2026 school budget of about $70 million would have grown to $73.9 million at 5 percent and to $77 million before reductions, Ross said, calling that trajectory “not really sustainable.”

Schools and town departments both moved, he said. The Schools, under Superintendent Frank Hackett and the School Committee, reduced 32.5 full-time-equivalent positions through layoffs, closing openings and not backfilling, raised fees in targeted areas, leaned on eligible reserves such as the Circuit Breaker, and pursued outside revenue. Town departments froze hiring of open fire department roles, pushed out the purchase of a police cruiser, reduced and delayed equipment purchases, trimmed the library’s spending increase, drew on the Finance Committee’s reserve fund, accepted a Select Board reduction to a 5-Tier benefit and cut DPW summer help and equipment.

On the revenue side, Ross said tax revenue (property, new growth, water and sewer) is projected to grow 3 percent from $11.9 million to $12.2 million, state aid 5.2 percent from $13.4 million to $14.1 million, and local receipts to come in at $13.7 million in the proposed FY27 budget against actuals trending to about $14 million in FY26. Across nearly every category, he said, the expense curve is still running north of 3 percent — faster than revenue.

Returning to a Top Gun reference he used on his first night as chair, Ross described the town’s estimated $21 million in free cash and a $10 million reserve floor as the “hard deck.” “In the movies, of course, he goes under, he pulls his F-14 up and it magically survives. But our financials aren’t as good as that F-14,” he said. Once spending breaks through the reserve floor, he said, the consequences are mass layoffs, immediate override pressure and cuts to services.

Ross said the FY27 budget totals about $171 million with 100 percent alignment between the Finance Committee, the Town Manager and the Schools, settling on a 4.4 percent school increase and using approximately $3.2 million in free cash to balance — in line with the $3.6 million ultimately used last year against an original $3.3 million target.

He acknowledged the three Finance Committee members who voted against the 10-3 recommendation. “They are not wrong,” Ross said. A sustained structural deficit puts the town’s ability to meet its needs at risk and forces short-term mitigation at the expense of long-term investments, he said.

He closed with three asks: approve the budget as is; commit to ongoing strategic long-term planning — “call it state of the town, call it whatever it needs to be” — on a one-to-three-to-five-year horizon, on both revenue and expenses; and on every future spending or borrowing vote, ask “what will this be at potentially the expense of?”
Town Meeting opens with recognitions for Eagle Scouts and All-American wrestler
Three Winchester High School seniors honored at Town Meeting
Kai Napadow Baquero, center, with Eagle Scouts Madison von Mering and Isabella Bogovich. Renee Lubomirski not pictured. Winchester News staff photo / Will Dowd
Moderator Phil Frattaroli opened Session 4 by recognizing four Winchester High School seniors, among others, for achievements outside the auditorium.

Kai Napadow Baquero was honored as an All-American wrestler. Madison von Mering, Isabella Bogovich and Renee Lubomirski were recognized as the first three girls in Winchester to earn the rank of Eagle Scout. Lubomirski was not present.
Session 3 · Monday, May 4
Session 3 recap: Forest Ridge defeated, K-5 literacy curriculum funded; budget pushed to Thursday
For the full account of Monday night’s session, read Chris Stevens’ coverage in Winchester News: “Winchester Town Meeting votes down Forest Ridge, says yes to new literacy program.”

The headline votes from Session 3:
  • Article 26 (WHS concrete repairs) — Indefinitely postponed by voice vote after the Educational Facilities Planning and Building Committee reported the problem was less extensive than feared and roughly $250,000 in summer repairs can proceed without new appropriation.
  • Article 28 (K-5 literacy curriculum / Arts and Letters) — Passed unanimously by voice vote. $598,540 from free cash for a K-5 curriculum across all five elementary schools. Finance Committee 13-0; Select Board and School Committee unanimous.
  • Article 29 (FY27 operating budget) — Postponed to a time certain (Thursday) by unanimous voice vote.
  • Article 33 (Personnel Board) — Postponed to a time certain at the Personnel Board’s request, by unanimous voice vote.
  • Article 34 (WCCP FY27 CPA budget) — Passed unanimously by voice vote. Select Board recommended unanimous favorable.
  • Article 35 (Forest Ridge / Forest Circle conservation purchase)Defeated 59-105 on an electronic vote; two-thirds was required. The motion would have authorized $3 million in borrowing to acquire roughly 13.5 acres off Forest Circle, with about $28,500 from CPA funds. Select Board, Finance Committee and Capital Planning all opposed; WCCP supported 7-1-1. A friendly amendment to lower the price to $2 million was ruled out of order. With motion one defeated, the second motion was declared irrelevant and the article concluded.
  • Article 38 (free cash / overlay to reduce the tax levy) — Moved to the fourth order of business Thursday by unanimous consent, since it requires the budget to be taken up first.
  • Article 39 (Transfer Station Data and Resource Committee, citizens petition)Passed 84-65 on an electronic vote. Establishes a one-year volunteer committee to analyze and report transfer station data. Select Board had opposed.
  • Article 40 (sidewalk snow-clearing bylaw, citizens petition) — Referred to the Select Board for further study on a voice vote rather than voted up or down. Petitioner Shamus Brady modeled the bylaw on Arlington’s. Select Board took no position; Finance Committee 8-0 unfavorable on enforceability concerns; School Committee 5-0 favorable.
  • Article 41 (anticoagulant rodenticide restriction, citizens petition) — Passed unanimously by voice vote. Restricts use of anticoagulant rodenticides on town property, with an emergency override provision. Select Board, School Committee 5-0, Finance Committee 7-1 and the Conservation Commission (unanimous on April 14) all favored.

Articles 36 and 37 were noted as part of the consent agenda but the transcript shows no separate roll call on them in this session. Town Meeting reconvenes Thursday, May 7 at 7 p.m. at Winchester High School to take up the FY27 operating budget and remaining articles.
Session 2 · April 30
10:20 p.m.
Town Meeting adjourns; budget waiver clears the way for next Thursday
Town Meeting adjourned around 10:20 p.m. after voting to waive the seven-day delivery requirement so the FY27 operating-budget motion book can be taken up later in the coming week. Moderator Phil Frattaroli had flagged the waiver at the start of the night, saying the budget would be moved off the traditional first Monday in May to give members closer to a full seven days to review materials before the vote. Members reconvene for Session 3 on Monday, May 4 at 7 p.m. at Winchester High School.
Town Meeting unanimously approves $1.5 million Muraco feasibility study
Town Meeting passed Article 27 unanimously on a voice vote, authorizing $1.5 million in borrowing to launch a Massachusetts School Building Authority feasibility study for Muraco Elementary School — the last of Winchester’s five elementary schools yet to be rebuilt or comprehensively renovated. A motion to adjourn before the article was taken up failed on a voice vote.

School Committee Chair Tim Matthews of Precinct 1 opened the presentation, saying Muraco is the final piece of a decades-long arc of school facility improvement and that an MSBA partnership has previously helped defray costs at Lynch, Vinson-Owen and Winchester High School. He noted Winchester’s relatively high community-income status caps the MSBA reimbursement rate at 32.47 percent for Muraco.

School Committee member John Bellaire of Precinct 2, a Muraco alum, said the building, constructed in 1967 on Bates Road, serves about 300 students in the northeast corner of town and has the second-highest concentration of high-needs students of any Winchester elementary, with about 40 percent of students designated as high needs and 11 percent low income. Muraco is a Title I school. He said MSBA invited Winchester into the eligibility period in December 2025 because Muraco is one of the lowest-quality elementary buildings in the state, citing aging structural systems, boarded-up windows, deteriorated brickwork, poor thermal performance and a basement that has been unusable since flood damage. Bellaire said the article authorizes the feasibility study only — one component of Module 1 of a nine-module MSBA process — and that an opening as soon as fall 2031 is possible if the town stays on schedule.

Select Board Chair Anthea Brady said the board voted 4-0-1 favorable, with one abstention. Brady recapped 2025 summer improvements: asbestos abatement and replacement of original carpets with VCT tile, and reconfiguration of the building’s “cafegymatorium” into separate cafeteria and gym spaces. Those changes did not address single-pane windows, original 1960s open-plan classroom design, broken curtain fixtures or basement mold, she said. The borrowing will be carried initially as short-term notes with small payments and rolled into a future debt-exclusion question once the MSBA reimbursement rate is set.

Finance Committee Chair Derek Ross said FinCom voted 9-0 favorable. “Look forward to a robust study of all options,” Ross said. Educational Facilities Planning and Building Committee member Christian Nixon of Precinct 1, a co-sponsor and a frequent floor presence this week — he moved the Monday amendment that added Ambrose Elementary to the Article 16 solar package — said his committee voted unanimous favorable. Nixon opened with a joke about the carriage house debate that had just ended (“How many people thought I was going to say something about the carriage house?”) before turning to Muraco. Nixon said the 2016-17 master plan prioritized rebuilding both Lynch and Muraco; MSBA invited Winchester in for Lynch first, after which the town developed a Muraco life-extension plan with the Select Board’s support, committing to a new Muraco underway between 2028 and 2030. He said the master plan’s Phase 2 visioning step had been paused during the override campaign and will resume after Town Meeting.

Joanna Shea O’Brien of 41 Lincoln Street, who said she has spent nine years on Muraco’s health and safety committee, was given the floor by unanimous consent. She told members the building’s auditorium doubles as the gym, students do individual work at tables in hallways and the lower level has been unusable for years after flood damage. She noted Town Meeting approved the Lynch feasibility study 131-7 in 2020 and asked members to do the same for Muraco. “Morocco parents have shown up for every school initiative in this town,” she said. “Tonight, we’re asking you to show up for us.”

Meredith Mason-Crowley of Precinct 1, a retired teacher, urged a yes vote. “The Muraco children all know that their school is next,” she said. “What we do here tonight will be a very powerful message to them.” She said delaying the vote to the November session would amount to saying no.

Frattaroli read the full motion authorizing the $1,500,000 borrowing for the feasibility study at 33 Bates Road. The article passed unanimously on a voice vote; two-thirds was required.
Read the motion (Article 27 from the Motion Book)
Read the Muraco feasibility study background and motion
Sanborn carriage house gets a reprieve: Town Meeting rejects $300,000 demolition, 61-89
The Sanborn House carriage house at 21 High Street
The carriage house at 21 High Street. Winchester News file photo
The Sanborn carriage house exterior
The Historical Commission deemed the building historically significant and imposed a 12-month demolition delay in August 2025. Winchester News file photo
Town Meeting rejected Article 25 by an electronic vote of 61-89 with seven abstentions, falling well short of the two-thirds needed to fund demolition of the Sanborn carriage house at 21 High Street — an Ambrose Elementary outbuilding the Winchester Historical Commission deemed “historically significant” in August 2025 when it imposed a 12-month demolition delay. The Select Board, School Committee and Capital Planning Committee all co-sponsored the article favorably; the Finance Committee recommended unfavorable.

Stefanie Mnayarji of Precinct 5, presenting for the School Committee, said the recommendation came “with a heavy heart” but that years of deferred maintenance had left the town with no practical use for the building. She said the carriage house sits on an active school campus along a state-designated safe route to school, ruling out housing or community-center reuse, and that recent visits had turned up evidence of trespassing, including drug paraphernalia, condom wrappers, can openers and a high chair that had moved from inside to outside the structure. She said a 2022 article to renovate the building for $6 million was rejected by 84 percent of Town Meeting and that construction costs have only risen since.

Select Board Chair Anthea Brady said the Select Board co-sponsored Article 25 and voted favorable action. Finance Committee member Gerard Sheehan of Precinct 3 said FinCom voted unfavorable to give the Winchester Historical Society a year to try to raise the money to repair the carriage house. Capital Planning Committee Chair Roger McPeek said the issue has been before the town in some form for more than 20 years. “There’s no joy in this. There’s nobody happy about any of this,” he said, adding that leaving the building standing carries its own costs — about $3,000 a year in insurance plus the risk that vandals could disturb contained asbestos and turn a manageable hazard into a fully contaminated structure.

William Swanton of Precinct 5, a board member of the Winchester Historical Society, said the society wants the building reused, possibly as a single-floor exhibit, lecture and performance space — an approach that would avoid triggering full ADA upgrades on all three floors and bring the cost down sharply from earlier multimillion-dollar plans. He said an email he had sent to Town Meeting members earlier in the day laid out the case and asked members to vote no to give the Historical Society time to develop a plan and raise private money.

Norah Cooney of Precinct 5, who lives on Oneida Road about 50 yards from the carriage house, said her children walk past the building twice a day on their way to Ambrose. She urged Town Meeting to fund the demolition. “The same way you have to secure a pool, even if someone hasn’t drowned in it yet,” she said. “This is a known hazard.” She said the project would have been better tackled a decade ago but that delay has only made the eventual cost higher and the risk worse.

Robert Colt of Precinct 6, a longtime Winchester Historical Society board member, urged a no vote. “This town should not be demolishing assets that are historical,” he said. He told members the Historical Society needs six months to a year to develop a private fundraising plan and pointed to the society’s renovation of the Sanborn House itself as proof the work can be done.

Select Board member Michelle Prior of Precinct 4, who said she was speaking as the former Select Board chair, urged a yes vote. She said the Select Board, School Committee and Capital Planning had intended to bring the demolition to fall 2025 Town Meeting, held off when the Historical Commission imposed its August demo delay, and was now taking it up 10 months later. The funding source is the Capital Stabilization Fund, not free cash, she said, and the building remains a liability the town carries even though it does not own it. “The time was probably 20 years ago, 10 years ago, or let’s say, August of 2025,” Prior said.

Susan DeLeo of Precinct 5, who lives on Tap Drive directly opposite the Ambrose driveway, said she supported the article. She said her children grew up being told to stay away from the building when riding bikes to the school, and that running an Ambrose gardening program next to the carriage house had repeatedly required steering students away from it.

Caitlin Musto of Precinct 4 said she also supported demolition, calling the late-arriving reuse plan “half-baked” and arguing that 24 years of inaction had already shown a viable plan would not materialize. “The question before us is not whether we spend the money, but when and how much,” she said.

Jason Roeder of Precinct 5, a new Capital Planning Committee member speaking for himself as an Ambrose parent, urged a no vote. He said he visited the Winchester Police Department earlier in the day and learned the only on-record incident at the carriage house was a single door-alarm activation about two years ago that turned up nothing. “It is not at all clear to me that this is a hazard different than it has been for many, many years,” he said. He said the Historical Society has shown willingness to lead a private fundraising effort and that the Finance Committee’s unfavorable recommendation pointed to higher-priority needs such as the Town Hall bell tower.

Vincent Dixon of Precinct 3 compared the carriage house to the Sanborn House — “a salt and pepper shaker” built by the same hands — and pointed to the Stone Zoo and Franklin Park Zoo as examples of public assets saved through 501(c)(3) hybrid structures. “We have the choice here to not go the way of Scollay Square, where beautiful buildings were torn down and people say, well, we didn’t like the bad buildings, but we lost the good buildings,” he said.

Marilyn A. Gagalis of Precinct 1 asked, “Why now?” She argued the funds could be used elsewhere given the failed override and that the Historical Society and Historical Commission have said the building is safe. Mnayarji answered with a slide titled “Why now?” pointing to a hole in the roof that has grown to the point that students on the third floor of Ambrose can see a family of raccoons coming and going, increasing vandalism and conditions that are not improving.

School Committee Chair Tim Matthews of Precinct 1 corrected the record on the building’s history: it was 2022 spring Town Meeting — not 2016 — that rejected a $6 million rebuild plan to relocate the Winchester Public Schools central office to the carriage house, with 82 percent of members voting no.

Amy Beliveau of Precinct 7, who said she had recently visited the building with a contractor, a School Committee member and a Historical Commission member, supported demolition. She told the meeting joists holding the roof and ceiling have been cut into and compromised, that there is graffiti, asbestos and mold inside, and that squatters had been confirmed to have lived in the basement. She said that of the 114 Town Meeting members still in the room from the 2022 vote, only 18 had voted to save the building, that no Friends-of-the-Carriage-House organization had formed in the years since and that no private money had been raised until that morning.

Michelle McCarthy of Precinct 7, a Historical Commission member, urged a no vote. She said the building is structurally sound and on the National Register of Historic Landmarks, and that a recently formed group has lined up pledges and donors to fund a private renovation. “The Historical Society is asking to not spend your money,” she said. “We’re going to save you money.”

Select Board member Paras Bhayani of Precinct 8 closed the supporters’ case. He said all five Select Board members signed onto a school-asset article only after a working group convened by the Historical Commission — with members of the Planning Board, School Committee, Mnayarji and Bhayani — explored reuse options that proved impractical given the safe-school-routes and access constraints. He said the president of the Winchester Historical Society had told the Winchester News the society’s focus was on raising $2 million for the Sanborn House itself and that it did not have the capacity to take on the carriage house. He warned that without demolition, Community Preservation Act funds — which the town just established — would be diverted to the carriage house instead of higher-priority projects.

A non-Town-Meeting-member resident at 247 Washington Street was given the floor by unanimous consent and urged a no vote: “Once we lose this, we cannot recreate it.”

A motion to close debate passed 105 votes to a handful (the threshold was 103, two-thirds). Members then voted on the appropriation itself: 61 in favor, 89 against, seven abstentions. Two-thirds was required. The motion failed and the carriage house remains standing. While the clickers were tallying, Frattaroli filled the silence by joking that he would “take this opportunity to make fun of Chris Nixon.”
Read the motion (Article 25 from the Motion Book)
Town Meeting doubles strategic capital maintenance fund to $200,000
Town Meeting passed Article 24, appropriating $200,000 from free cash to a Strategic Capital Maintenance Fund effective July 1. The fund, in place since 2015, is meant to fill the gap between routine maintenance and major capital replacement projects, letting staff move quickly on repairs that fall outside the normal capital cycle. The town manager administers the account in consultation with the Capital Planning Committee. The previous standing appropriation was $100,000 a year; this year’s motion doubles it.
Read the motion (Article 24 from the Motion Book)
$3.2 million green-lit for South Reservoir Dam, Town Hall roof and bell tower
Town Meeting approved Article 21, an additional $830,000 in funding for repair and construction at the South Reservoir Dam — a state-regulated structure where deferred maintenance carries legal and financial consequences. Members also approved Article 22, $2.4 million in additional funding for roof repair and construction at Town Hall and the Town Library, renovation of the Town Hall bell tower and replacement of library windows. The Article 22 package combines $1.4 million from the Building Stabilization Fund with $1 million in borrowing. Both articles required a two-thirds vote.
Read the motion (Article 21 from the Motion Book)
Read the motion (Article 22 from the Motion Book)
ADA, stormwater compliance and Everett Avenue flooding clear $325,000 hurdle
Town Meeting passed Article 19, funding three FY27 capital projects totaling $325,000 effective July 1: $125,000 from the Capital Stabilization Fund for the town’s ADA Transition Plan (majority vote), $150,000 for MS4 federal stormwater permit compliance — $9,800 from an existing MS4 account and $140,200 from Water & Sewer Retained Earnings — (two-thirds vote), and $50,000 from Water & Sewer Retained Earnings for engineering analysis of Everett Avenue area drainage (two-thirds vote).

Brian Vernaglia of Precinct 4, presenting on behalf of the Capital Planning Committee, said the ADA Transition Plan dates back 16 years and that more than $3 million in projects remain to bring Winchester into compliance, with prices rising every year the work is delayed. He said the MS4 funding represents year one of a new five-year stormwater compliance cycle. He said the Everett Avenue money will pay for an engineering assessment and flood modeling after residents shared videos of street-level flooding near the boat-club culvert during high-volume storms; the work is meant to ensure any future culvert repair is right-sized.

Select Board member Anthea Brady said the board voted unanimously in favor of all three motions. Finance Committee member Gerard Sheehan of Precinct 3 said FinCom also recommended favorable action on all three motions. Each motion passed unanimously on a voice vote.
Read the motion (Article 19 from the Motion Book)
Capital Planning chair sets the table; longtime Winchester fixture Helen Philliou steps off the committee
Capital Planning Committee Chair Roger McPeek told members the committee would move quickly through the night and previewed the remaining articles in the committee’s slate: South Reservoir Dam supplemental funding, the Town Hall roof and bell tower work, the Town Hall design and development documents (which the committee had considered pulling but will move forward with) and the Carriage House demolition. He welcomed Jason Roeder of Precinct 5 as a new member of the committee, replacing longtime member and former chair Helen Philliou, who McPeek said served Winchester for more than 30 years across Town Meeting, the Finance Committee and Capital Planning. Town Meeting voted to receive and file the Capital Planning Committee’s FY27 report.
Read the Capital Planning Committee FY27 report
Robert’s Rules out: Town Meeting adopts ‘Town Meeting Time’ and codifies its own playbook
Town Meeting made quick work of Article 5, adopting a package of parliamentary updates co-sponsored by the Special Town Meeting Committee and the Committee on Rules.

Laura E. Colella of Precinct 2, who represented the Committee on Government Regulations on the special committee, presented the article. She walked members through the history: Town Meeting referred a parliamentary-rules change to study at the 2025 spring session, a Parliamentary Rules Study Group reported in summer 2025 recommending Winchester adopt “Town Meeting Time”, and the 2025 fall Town Meeting then charged the Special Town Meeting Committee — Moderator Phil Frattaroli, former moderator Heather von Mering, study-group representative Susan DeLeo, Committee on Rules representative Brenda Mandile and Colella — with resolving the open procedural questions. The committee met several times over the winter and spring with Town Counsel Karis North.
Read the revised motion (Article 5 Revised Motion PDF)
Colella said the article does four things: it replaces Robert’s Rules of Order with “Town Meeting Time” (Section 3.1); codifies the assistant-moderator role and clarifies that the assistant moderator has no authority to run the meeting in the moderator’s absence (Section 3.2); writes Winchester’s “Move the Vote” practice into the bylaws so members can call for the vote without queuing at a microphone, with the moderator’s discretion to delay it, and bars a member from interrupting a speaker or moving the vote immediately after their own remarks (Section 3.6); and codifies the consent agenda already in use, including who reviews articles for inclusion and how items can be removed (Section 3.10.24). She said additional Winchester practices that do not require a bylaw will be written into an updated “Guide to Winchester Town Meeting”.

Bill McGonigle of Precinct 3, delivering the Select Board recommendation, said the board voted unanimously in favor and looks forward to seeing the updated guide ahead of fall Town Meeting. Brian McCarthy of the Committee on Rules said his committee unanimously recommended favorable action, calling the changes more efficient while preserving Winchester traditions. Committee on Government Regulations Chair Stephen Boksanski said his committee also voted unanimously in favor.

Town Meeting passed Article 5. The bylaw changes will go to the Massachusetts Attorney General’s Office for review and approval before taking effect, with the goal of having them in place for the fall 2026 Town Meeting.
Winchester gets a Human Rights Commission, 124-29
Town Meeting picked up Article 4, the proposed bylaw to create a nine-member Human Rights Commission, at the start of the Thursday session. Moderator Phil Frattaroli opened the night noting an injury and a tight schedule, and laid out a plan to take up Articles 4 and 5 first, then move to capital planning Articles 17 through 24 before a break. He said the operating budget will be taken next Thursday rather than the usual first Monday in May, with a waiver of the seven-day requirement so members still have time to review.

Select Board Chair Anthea Brady presented Article 4, saying the proposal grew out of a fall Town Meeting commitment and was developed by a working group that included a School Committee member, the town clerk, the Network for Social Justice and several residents. She said the commission would serve as a point of contact for residents, refer people to resources, host or partner on educational programs, review bylaws and policies affecting residents’ human rights, and report annually to Town Meeting and twice a year to the Select Board and School Committee. The body would have nine members — four residents, two high-school students serving one-year terms, a senior School Department administrator, a town manager designee and a police designee — with appointments split among the Select Board, School Committee and superintendent. Brady said the article has no direct budget impact and does not draw on free cash or borrowing.
Read the revised motion (Article 4 Revised Motion PDF)
Rebecca Slisz, executive director of the Network for Social Justice and a Precinct 8 Town Meeting member, cited statewide data showing 3,243 new discrimination complaints filed with the Massachusetts Commission Against Discrimination in 2025, 467 hate crimes reported in 2024 and a 23 percent increase in antisemitic incidents from 2023 to 2024. She said local youth health survey data shows Winchester middle and high school students from marginalized identities report being bullied or feeling unsafe at statistically significant rates, and read a comment the network has heard through its Response and Advocacy Committee: “Racism can be taken lightly by people who aren’t affected by it, and it’s hard to get people to pay attention to the problem.”

Slisz said Winchester’s 2009 human rights statement, updated in 2020 to add country of origin and immigration status, is not enough on its own. “Multiple things can be true at the same time,” she said, arguing that discrimination exists in Winchester and that a commission would deliver on the values in the statement. She said the network and a commission would be complementary, not duplicative, and pointed to Belmont, Arlington and Hingham as nearby towns where commissions and community partners run educational programs together. “We need more partnerships like this, and more people doing this work, not fewer,” she said.

The Select Board, School Committee, Board of Health and Housing Partnership Board have all voted favorable action. The Chinese American Network of Winchester, Network for Social Justice and Winchester ABC are among the community organizations backing the article.

Committee on Government Regulations Chair Stephen Boksanski (Precinct 4) said his committee voted 8-0 unfavorable, but stressed the objection is procedural rather than about the merits. Citing Town Charter Section 2-11, he said standing committees of Town Meeting are defined narrowly as bodies to which “shall be referred warrant articles for study, review and report in advance of the sessions of the town meeting,” and that the proposed commission’s point-of-contact, education, subcommittee and policy-monitoring duties go well beyond that role. “It’s a square peg trying to fit into a round hole,” Boksanski said, and suggested the commission could instead be created by Town Meeting vote outside the bylaws, as many existing advisory committees are.

Brady responded that the revised motion already addresses the concern. She said the commission is no longer being established as a Section 2-11 standing committee but as a new chapter in the Code of Bylaws, and that the word “jurisdiction” has been replaced with “purview” to clarify ambiguous wording.

Amanda Lewis of Precinct 1, president of Winchester ABC, was the first floor speaker, urging support. “The statement is only as strong as the tools we create to uphold it,” she said, pointing to programs in Lexington, Arlington and Dedham, including “No Hate November” campaigns and local channels for residents to report bias incidents before they escalate. “It would not just be a reactive body,” she said of the commission. “It would be a proactive classroom for our community.” Lewis said the body would host public forums on fair housing, lead workshops on recognizing implicit bias and partner with schools to bring civil rights history into classrooms, and noted Winchester ABC’s 54-year history of bringing scholars of color to town. “This commission allows us to do more than say we are a welcoming community,” she said. “It does something to show that we are one.”

Maura Sullivan followed, saying she had risen to argue the commission belonged in Chapter 2 as a standing committee but was satisfied with its placement in a new Chapter 27. She pointed to Section 2.5 of the bylaws, which says Town Meeting may establish committees as it deems appropriate so long as they are not inconsistent with law, and said the original framing would not have conflicted with the charter, the bylaws or state law.

Incoming Board of Health Chair Shannon E. Scott-Vernaglia said the board voted unanimous favorable action. She said the work aligns with the Coalition for a Safer Community, housed within the Department of Public Health, and that the Youth Risk Behavior Survey shows rising mental health concerns among gender-minority and ethnic-minority students. “We feel this is a really important piece to kind of continue to support the work that many different groups in town are doing,” she said.

Megan Blackwell of Precinct 7, a member of the Committee on Government Regulations, asked Brady whether the Select Board could create the body as an advisory committee on its own if Article 4 failed. “Generally, there’s always another way,” Brady said. “The vote tonight is to establish this committee versus not establishing this committee, and not to establish this committee in deciding how it will be established.”

Roger Wilson of Precinct 1 asked about the cost of providing access to Town Counsel and of having the town manager or a designee keep minutes. Brady said the Select Board has discussed using AI tools such as Otter or Zoom recordings — already in use by other boards — as a no- or low-cost way to manage minutes. She said the town manager closely manages access to Town Counsel and would continue to do so for the commission “so that Town Counsel’s time would be used appropriately and not excessively.”

Colin G. Simson of Precinct 5, also a member of the Committee on Government Regulations, said he supports establishing a Human Rights Commission but not as a bylaw, citing the long list of advisory committees doing similar work outside the bylaws. He moved that Town Meeting not endorse Article 4 as a standalone bylaw and ask the Select Board to establish the commission as a committee of the Select Board instead. Frattaroli ruled the motion out of order.

Jennifer Infurna of Precinct 3 asked whether the Committee on Government Regulations had re-voted on the revised structure since Brady said the standing-committee framing had been removed. Boksanski said the committee did not formally reconvene under Open Meeting Law but that he had polled members individually. “We all felt the same way: that we endorse the idea,” he said. “We just don’t think the bylaws is the right place for it.” He said Section 2.5 of the bylaws allows Town Meeting to establish committees, and that most such committees in Winchester operate effectively without being written into the bylaws.

School Committee Chair Tim Matthews of Precinct 1, who said he was speaking as a Town Meeting member rather than in his school or Network for Social Justice trustee roles, told the meeting his family has been targeted by anti-LGBTQ bias in Winchester. He recounted that three years ago, while he and his then-six-year-old son were walking to their car after a Network for Social Justice Pride Fest, teenagers in a Jeep drove by and screamed a slur at his son. He said he has personally experienced two anti-LGBTQ bias incidents since moving to Winchester in 2018. Matthews said a Human Rights Commission was previously in the town’s bylaws with a sunset provision in the mid-1980s and that similar bodies are written into bylaws across the Commonwealth. “I think it is a material and egregious omission that our town does not have this,” he said. He asked Brady about the research behind the proposed structure and asked Town Counsel Karis North to address how peer communities have handled their commissions.

Brady said the working group consulted Stoneham, Arlington, Belmont and Lexington, and that Rebecca Slisz brought contacts at the Massachusetts Human Rights Coalition. She said the structures vary — some communities establish their commissions by bylaw, some do not — and that Winchester would not be a “unicorn” in doing so. “It is more than a town meeting committee,” Brady said. “As a Human Rights Commission, it should be elevated to the level of a bylaw, and it needs the structure of the bylaws, which go beyond that of a simple committee that could be formed and unformed, or, you know, change over time.”

North told the meeting that one of the communities she represents has a Human Rights Commission and that the use of such commissions has been “swinging back” as more towns reconsider bodies they once dissolved. She said putting the commission in the bylaws is appropriate and gives the public clear notice. “Anybody who looks to see what they can and can’t do in the town of Winchester sees it in the bylaws,” she said. “If it’s just a town meeting committee or a committee of the Select Board, it’s a lot harder to find that information.” Matthews briefly returned to the microphone to say being in the bylaws “matches the gravity of the issues that are at play here.”

A Precinct 5 member asked Brady what would actually be different if the commission were created outside the bylaws. Brady said the difference is largely visibility and the elevated status of being written into the code.

Christian Nixon of Precinct 1 said he supports the article but had questions about how a Human Rights Commission would engage with minors, given that the body would itself include two student members and would meet in public. He asked Matthews and Superintendent Frank Hackett how the commission would interact with school policies, complaints involving students and student privacy expectations. Matthews said the School Committee voted 5-0 in favor of both the original and revised language and described the commission as a coordinating body that could pull together police, schools and town leadership when an issue crosses silos. He said student-privacy laws would still apply. Brady said an FAQ released with the article anticipates the question and that the commission would develop an intake process that respects FERPA, makes use of executive session where appropriate and redacts records when necessary.

Catherine Bauer of Precinct 8, a first-time speaker who said she works in professional conduct at a university, urged support. “There’s a lot of discrimination that happens, maybe under the radar, if you’re not in that category that’s being discriminated against,” she said, and asked that the commission ensure intake is handled by someone trained for sensitive cases.

Michelle McCarthy of Precinct 7 asked about the financial impact and whether the town would be paying staff time, including the police chief’s. Brady said there is no direct financial implication and that any work by the three town employees on the commission — the school administrator, the town manager designee and the police designee — would be within the scope of their existing positions.

Michael Galvin of Precinct 2 asked which boards had voted on Article 4. Brady said the Select Board, School Committee, Housing Partnership Board and Board of Health all voted unanimously in favor, and noted, after a prompt, that the Committee on Government Regulations voted unanimously against.

Diab Jerius of Precinct 8 said he supports placing the commission in the bylaws because the work is too important to depend on the priorities of any single Select Board. “I don’t trust government,” he said. “If something is important to a community, it should be a part of the structure of government, and not be at the whim of a committee.” He warned of a potential conflict of interest if the commission were a Select Board subcommittee and the Select Board itself were the subject of a complaint.

Select Board member Paras Bhayani of Precinct 8 said every town bordering Winchester has a commission — Lexington’s dating to 1963, Stoneham’s the newest in 2019 — and that roughly half were established by bylaw. He said Town Counsel and the revised motion both confirm a bylaw approach is permissible, and that permanence, visibility and the involvement of multiple boards (Select Board, School Committee, Disability Access Commission, Council on Aging) argue for the bylaw route. “On the other side, all we’re hearing is, well, we don’t really know why it needs to be, so therefore it shouldn’t be,” Bhayani said.

Meredith Mason-Crowley of Precinct 1, also a member of the Committee on Government Regulations, closed the debate by saying the committee supports a Human Rights Commission but that, of the peer towns reviewed, more operate their commissions by policy than by bylaw or ordinance.

Town Meeting passed Article 4 by electronic vote, 124-29, establishing a nine-member Human Rights Commission as a new chapter in the Code of Bylaws. Like Article 5, the bylaw will go to the Massachusetts Attorney General’s Office for review and approval before taking effect.
Session 1 · April 27
Town Meeting adjourns; reconvenes Thursday at 7 p.m.
Town Meeting adjourned for the night after Article 16, before the Capital Planning Committee could begin its presentation under Article 17. Members will reconvene Thursday, April 30, at 7 p.m. at Winchester High School to pick up where they left off.

The Monday session moved through Articles 1, 3, 6, 7 and 8 before voting Article 15 down from $1 million to a $750,000 stabilization fund deposit and passing Article 16 — the $7.943 million solar bonding authorization — with a floor amendment adding Ambrose Elementary as a sixth eligible site. Articles 4 and 5 were postponed to Thursday at the start of the night, and the consent agenda has not yet been taken up.

Thursday’s session is expected to take up the Capital Planning Committee’s revised FY27 capital plan, among other articles.
Town Meeting passes Article 16 solar project
After the longest debate of the night, Town Meeting passed Article 16, authorizing $7.943 million in borrowing to install town-owned solar panels — expanded from five sites to six on the floor.

Town Meeting member Chris Nixon moved a friendly amendment to add Ambrose Elementary (27 High Street) to the list, citing the same structural engineer who worked on Lynch and noting the school’s suitability for solar. Adding Ambrose does not obligate the town to install there but makes funds available to study the site. The Select Board endorsed the amendment unanimously, 5-0, and the School Committee supported it. The amendment passed on an electronic vote.

Sustainability Director Ken Pruitt and Energy Management Committee member Mike Bettencourt presented the underlying project, telling members the town stands to lose $2 million in federal tax incentives and a $1 million state climate leader grant if Town Meeting did not authorize the borrowing now. They projected total energy savings of more than $16 million over 25 years, with first-year net savings of about $100,000 and an average of about $300,000 per year thereafter.

The original sites remain Winchester High School (rooftop and parking canopy), McCall Middle School, Vinson-Owen Elementary, the DPW and the Transfer Station, with Ambrose now added. Pruitt said the package is conceptual and that individual sites could still be modified or dropped if engineering review finds problems.

Members raised pointed questions about the structural capacity of the high school gym roof, the longevity of solar panels and inverters, whether battery storage was considered, and why other sites such as Town Hall and Jenks were ruled out. Pruitt said a 2018 engineering analysis supports placing arrays on the high school roof and that a full engineering review will be conducted before any installation. He said decommissioning costs at year 21 are funded in the project and that inverter replacement is included.

Select Board member Paras Bhayani defended the proposal, telling members it has been roughly 11 months in the making and was developed by a cross-functional working group that included representatives of the School Committee, the Energy Management Committee and the Finance Committee. Energy Conservation Coordinator Susan McKee said the Energy Committee voted favorable action and noted that more than 300 schools across Massachusetts have similar systems with low maintenance costs.

One speaker, Milan John, urged the town to focus instead on deferred maintenance such as Town Hall, citing a negative net present value at Lynch Elementary and questioning whether the project would deliver the projected returns.

The Finance Committee came to Town Meeting with a 6-3 unfavorable recommendation, with two members abstaining. FinCom Chair Derek Ross said members raised concerns about the timing given the town’s broader budget picture and questions about the net present value calculation. The School Committee is a co-sponsor and supports the article. The Select Board also recommended the article favorably. The amended article required a two-thirds vote to pass.
Town Meeting approves $750,000 stabilization fund deposit — amended down from $1 million
Town Meeting approved Article 15, depositing $750,000 from free cash into the General Stabilization Fund — less than the $1 million originally proposed.

Select Board Chair Michelle Prior moved to amend the motion on the floor, reducing the amount to $750,000. She said the board made the call after tallying current-year budget needs that will require free cash before the fiscal year ends, including snow and ice costs and Fire Department personnel expenses, and wanted to leave a larger cushion.

Prior said the General Stabilization Fund currently holds $5.4 million — rising to $6.1 million with tonight’s deposit — well short of the $10 million floor that Moody’s and the state Department of Revenue recommend. She said the Select Board wants to make incremental deposits each year until the fund reaches its target.

“We really haven’t done anything deliberately in all those years,” Prior said of past inaction on the fund.

Select Board member Paras Bhayani said the town’s total operating reserves — free cash plus the stabilization fund — should ideally be split 50-50, but Winchester is far from that ratio. He said the correct amount to eventually reach that balance would be closer to $13 million in the stabilization fund.

The Finance Committee came to Town Meeting with an 8-0 favorable recommendation, though members noted they would have preferred the higher amount. The article passed on a voice vote.
9:09 p.m.
Town Meeting approves 7 percent water and sewer rate increase
Town Meeting approved Article 8 on a voice vote, authorizing a 7 percent annual increase in water and sewer rates through fiscal year 2031.

Select Board member Anthea Brady presented the article, explaining that Winchester’s water and sewer system operates as a separate Enterprise Fund, funded by quarterly bills rather than the property tax levy. She said the 7 percent increase is in line with what the board planned in 2023 and 2024, and is driven largely by rising MWRA assessments and capital borrowing costs.

Brady said the average residential quarterly bill would rise about $16 — from $267.61 to $283.89 — with the increase split across MWRA assessments, operating expenses, debt service and indirect costs. She noted that summer weather patterns make revenues unpredictable, and said the town needs the increase to stay within its targeted range of retained earnings.

A Town Meeting member raised questions about the $35 quarterly service fee and how it was set. Brady said the fee is based on the estimated cost of operating and managing each meter annually.

The Finance Committee came to Town Meeting with a 7-2 favorable recommendation. The Select Board recommended the article 5-0. The article passed on a voice vote.
Town Meeting passes Article 7 — local occupancy excise tax
Town Meeting approved Article 7, imposing a 6 percent local occupancy excise tax on short-term rentals, including Airbnbs and VRBOs operating in Winchester.

Select Board member Paras Bhayani said the article grew out of the board’s State of the Town analysis and a search for non-property-tax revenue. He said Winchester is among the only peer communities not already collecting such a tax, and that the state was already collecting its own 5.7 percent tax from short-term rental operators in town.

The tax applies to rentals of about 30 days or less. Accessory dwelling units leased long-term would not be affected, but an ADU listed on Airbnb would be. Bhayani said the Department of Revenue estimated the tax would raise about $14,000 for the town annually, though state figures from fiscal years 2024 and 2025 suggest actual receipts have run closer to $15,000 to $17,000. The Finance Committee came to Town Meeting with a 7-2 favorable recommendation. The article passed on a voice vote.
Town Meeting passes Article 6 — Board of Health permit fees
Town Meeting approved Article 6, allowing the Board of Health to set and adjust permit fees for recreational camps for children without returning to Town Meeting each time.

A Board of Health representative said the change is straightforward: the town already issues annual permits to five to nine camps per year under state law, but updating the $200 fee has historically required a Town Meeting vote. The article simply shifts that authority to the Board of Health. The Select Board came to Town Meeting with a favorable recommendation. The Committee on Government Regulations recommended the article 8-0. The article passed on a voice vote without opposition.
Articles 4 and 5 postponed to Thursday
Town Meeting postponed Articles 4 and 5 to the Thursday session. Article 4 would establish a nine-member Human Rights Commission through a bylaw amendment. Article 5 would update Town Meeting’s rules of procedure, replacing Robert’s Rules with “Town Meeting Time” as the parliamentary authority and adding a consent agenda, electronic voting provisions and a seven-day motion delivery requirement.
8:35 p.m.
Town Meeting reconvenes after precinct meetings
Winchester Town Meeting reconvened at 8:35 p.m. following a break for precinct meetings, with members returning to continue work on the spring warrant.
8:35–8:45 p.m.
Planning Board chair outlines zoning work, downtown development and Article 3 context
Planning Board Chair Jack LeMenager outlined the board’s recent work on zoning, development and long-term planning, including projects tied to Article 3.

LeMenager said the Planning Board is responsible for proposing zoning bylaw changes and serves as the special permit granting authority for projects in key districts, including the Center Business District and MBTA overlay areas.

He highlighted the board’s recent approval of a five-story redevelopment at 10 Converse Place after months of public hearings and community input. The project includes 34 residential units, commercial space and public green space, and is expected to generate more than $500,000 annually in property taxes and about $7 million over 10 years.

LeMenager said the board is also reviewing a new proposal at 910 Main St., the site of the “pink building,” which could include housing, parking and commercial space, though design concerns remain.

He added that the town is working with a consultant to review and simplify zoning and special permit processes, with recommendations expected this summer and potential bylaw changes headed to fall Town Meeting. The Planning Board is also beginning a review of the town’s 2030 master plan as it prepares for the next long-range planning cycle.
8:05 p.m.
Town Meeting approves Article 1
Winchester Town Meeting approved Article 1, marking the first vote of the spring session. The article passed without extended debate as members moved through initial business following opening motions and procedural approvals.
Opening session
School Committee outlines budget cuts, staffing reductions and curriculum priorities
School Committee Chair Timothy Matthews said Winchester Public Schools are facing significant financial challenges, with planned cuts affecting staffing, programming and services.

Matthews said the district is continuing to implement a new K–5 literacy curriculum, Arts and Letters, following a multi-year review process. He said elementary math interventionist positions added last year are expected to be eliminated in fiscal 2027 due to budget constraints.

The district is projecting a 5 percent budget increase for fiscal 2027 but still expects layoffs and reductions. Officials are considering cutting about 22 positions in addition to previously planned enrollment-based reductions, affecting paraprofessionals, instructional staff, coordinators and central office roles.

Matthews said about 88 percent of the school budget is spent on salaries and benefits, leaving limited flexibility to reduce costs without affecting personnel. He also pointed to rising special education and transportation costs, along with state aid that has not kept pace.

“Winchester is not alone … in facing severe funding challenges,” Matthews said.
Town manager says Winchester is looking for new revenue, making cuts and protecting core services
Town Manager Chris Senior, speaking in his first spring Town Meeting in the role, said Winchester’s AAA bond rating was reaffirmed in February and that the town has received about $400,000 in municipal grants this year for water asset management, energy efficiency and recreation programming.

Senior said the town has reviewed building fees to bring them more in line with surrounding communities and is also evaluating transfer station fees, parking fees and fines.

“Penalties should dissuade people,” Senior said. “They shouldn’t be an easy way out.”

Senior said Winchester has identified roughly $1 million in reductions across municipal departments and undesignated accounts — including hiring freezes in the Fire Department and DPW, elimination of seasonal DPW workers, one fewer police cruiser than planned and a cut to the recreation subsidy. He said the reductions do not include layoffs of existing municipal employees but will have service impacts.

“We can’t not respond to a call. We can’t not plow a road,” Senior said.
Finance Committee chair says town is close to budget alignment but still faces structural deficit
Finance Committee Chair Derek Ross said Winchester is on track to meet or come close to its fiscal 2026 operating budget but continues to face an unsustainable structural deficit. He said officials are resolving about $900,000 in remaining items, putting the plan about 99.5 percent in alignment.

Ross said Winchester has about $21 million in free cash, with roughly $10 million considered a reserve floor to protect borrowing capacity. That leaves about $11 million in usable funds, though he noted at least $3 million is likely to be used soon.

“Be prudent on what we use and make sure it’s something we definitely need, and need now,” Ross said.
Select Board chair says failed override will require trade-offs
Select Board Chair Anthea Brady said Winchester is operating in a changed fiscal environment after voters rejected an $11.5 million operating override in March. She said the failed override carries consequences, including school staffing reductions, modest class-size increases and cuts to seasonal DPW staffing.

“This problem isn’t isolated to Winchester,” Brady said, noting similar override efforts in other Massachusetts communities.
Town Meeting approves opening motions
Town Meeting approved seven preliminary motions governing the session, including seating arrangements, adjourned session scheduling and cable coverage. Moderator Phil Frattaroli noted a scrivener’s error in Article 18, correcting the figure to $848,451.07.
7 p.m. — Session opens
Moderator opens Town Meeting with tributes and swearing-in
Moderator Phil Frattaroli opened Winchester’s spring Town Meeting by reflecting on the role of Massachusetts town meetings in the American Revolution. He led a tribute to three residents who have died since the fall Town Meeting: Kevin Mawn, John Lane and Bob Johnson. Members observed a moment of silence.

Frattaroli then swore in newly elected and re-elected Town Meeting members and recognized former Assistant Town Manager Mark Toohey, who retired after 44 years of service two years ago.

“For his decades of service to the town, we all owe him a deep debt of gratitude,” Frattaroli said.
Interactive tracker

All 46 warrant articles, explained

Tap any article to see what it does, who sponsors it and why it matters. This tracker will be updated in real time before, during and after Town Meeting — bookmark it and check back.

LIVE · Town Meeting under way · Updated May 6, 2026
Up next: Session 4 convenes Thursday, May 7 at 7 p.m. at Winchester High School to take up the FY27 operating budget (Article 29) and remaining articles. Session 3 (Monday, May 4) defeated the Forest Ridge conservation purchase (Article 35, 53-105), passed the $598,540 K-5 literacy curriculum (Article 28), passed the FY27 CPA budget (Article 34), passed the transfer station data committee citizens petition (Article 39, 84-65), passed the anticoagulant rodenticide restriction (Article 41), referred the sidewalk snow-clearing bylaw (Article 40) to the Select Board, and indefinitely postponed the WHS concrete repairs (Article 26). Articles 29, 33 and 38 were postponed to Thursday. For the full account, read Chris Stevens’ coverage in Winchester News.
Updated article sections now reflect revised Town Meeting materials and late clarifications, including:
Representative Town Meeting
Winchester uses a Representative Town Meeting — not an open town meeting. Only 192 elected Town Meeting members, divided equally among eight precincts (24 per precinct), may make motions and vote. Any resident may attend and speak but may not vote. A quorum of 100 members is required. The budget arrives against the backdrop of a failed $11.5 million Proposition 2½ override on March 21 and a projected $5.1 million deficit closed through cuts, new revenue and about $3.6 million in free cash.
Badge key:
Favorable Unfavorable No action Pending Passed Failed Amended Withdrawn Postponed TBD
On a phone, rotate to landscape for the best reading experience.
Border key: High stakes Notable Routine
Article
Title / key detail
Category
Vote
required
Select Board
rec.
Town Meeting
vote
Post-override budget context
Voters rejected an $11.5 million Proposition 2½ override on March 21. The fiscal year 2027 budget (Article 29) closes the resulting gap through approximately $750,000 in municipal cuts, $950,000 in school-side reductions, about $1 million in new revenue assumptions and a $3.6 million draw on free cash — a one-time reserve that must be replenished. Comptroller Stacie A. Ward has cautioned that reserves will be tight. The Select Board is signaling a possible November override question and has directed staff to explore additional fee increases and service restructuring.
Source: 2026 Spring Annual Town Meeting Warrant · Select Board meetings of March 30, April 6 and April 13, 2026 · town manager reports · Winchester Home Rule Charter