Winchester 2026 town election guide

This is a comprehensive, nonpartisan guide to the March 21, 2026 annual town election in Winchester, Massachusetts, produced as a collaboration between the League of Women Voters of Winchester and Winchester News. It is a living document. Content is added and updated as information becomes available. Neither the League of Women Voters of Winchester nor Winchester News supports or opposes any political party or candidate.

Election at a glance

The annual town election will take place Friday, March 21, giving Winchester voters the opportunity to choose officeholders who set policy, oversee town departments and manage the municipal budget. Polls will be open from 7 a.m. to 8 p.m. at the Winchester High School cafeteria, 80 Skillings Road, which will serve as the central polling location for all eight precincts.

How to vote

Register to vote: Voters must be registered by March 11, 2026. Registration status can be checked through the state's online voter registration system.

Vote by mail: Applications for vote by mail ballots are accepted and processed upon receipt. The deadline to apply is 5 p.m. March 16, 2026. Ballots must be completed and returned by 8 p.m. March 21, 2026 to be counted.

Absentee voting: Absentee ballots are available for voters who will be absent from town on election day or who qualify due to disability or religious belief. Ballots can be cast in the town clerk's office beginning March 2. The deadline to apply for an absentee ballot is noon March 20. Completed ballots must be returned by 8 p.m. March 21 to be counted. Applications and instructions are available through the Winchester annual election page.

Early voting in person: Early voting will be held at Town Hall, Winchester Room, first floor, 71 Mt. Vernon St. The schedule is as follows:

Voting on election day: Polls will be open from 7 a.m. to 8 p.m. Saturday, March 21, 2026 at Winchester High School cafeteria, 80 Skillings Road. All eight precincts will vote at this central location.

Debates and forums

The League of Women Voters of Winchester and Winchester News are collaborating to hold two candidate forums before the March 21 town election. Both events include informal meet-the-candidates opportunities for Town Meeting races in all precincts. Links to video recordings of candidate debates will be posted here once available from WinCam.

Thursday, Feb. 26
The Jenks Center, Cummings Room, 109 Skillings Road
6:30-7 p.m.: Meet Town Meeting candidates — all precincts
7-8 p.m.: Planning Board debate (two seats): Amy Beliveau, Keri Layton, Nicholas Rossettos

Thursday, March 5
The Jenks Center, Cummings Room, 109 Skillings Road
6:15-6:45 p.m.: Meet Town Meeting candidates — all precincts
6:45-8 p.m.: School Committee debate (one seat): John Bellaire and Heather K.R. Von Mering; Select Board debate (one seat): Shamus Brady and Michelle Prior

Candidates for townwide offices

The League and the Winchester News will send out questionnaires to all candidates running for townwide offices, asking about their backgrounds, qualifications and positions on key issues facing Winchester. Candidate profiles will be published according to the following schedule:

Feb. 2
List of candidates who submitted nomination papers published

Feb. 24
Deadline for candidates to submit profile information

Late April
All candidate profiles published online

Readers will be able to then click on a candidate's name below to read their biographical information and positions on key issues facing Winchester.

Select Board (one seat, three-year term)
— Michelle Prior (incumbent)
— Shamus Brady

The Select Board serves as the town's chief executive body, overseeing the town manager, setting policy priorities and managing Winchester's more than $100 million annual budget.

School Committee (one seat, three-year term)
— John Bellaire
— Heather K.R. Von Mering

The School Committee oversees Winchester Public Schools, approves the school budget, sets education policy and hires the superintendent.

Planning Board (two seats, three-year terms)
— Keri Layton (incumbent)
— Nicholas Rossettos (incumbent)
— Amy Beliveau

The Planning Board reviews and approves development projects, creates the master plan and oversees zoning changes to shape Winchester's physical development.

Board of Health (one seat, three-year term)
— Dr. Gregory Sawicki (incumbent)

The Board of Health protects public health through oversight of food establishments, housing inspections, disease surveillance and environmental health matters.

Board of Assessors (one seat, three-year term)
— Richard Michienzi (incumbent)

The Board of Assessors determines property values for tax purposes, reviews abatement requests and ensures fair and equitable property assessments across town.

Housing Authority (one seat, one-year term)
— Brenda Kleschinsky

The Housing Authority manages Winchester's public housing, oversees affordable housing programs and works to address housing needs for low-income residents.

Library Board of Trustees (two seats, three-year terms)
— Katherine Ho

The Library Board of Trustees oversees Winchester Public Library operations, sets library policy, approves the library budget and hires the library director.

Town Moderator (one seat, one-year term)
— Philip Frattaroli (incumbent)

The town moderator presides over all town meetings, maintains order during debates, rules on parliamentary procedure and ensures fair and efficient conduct of town meeting business.

Candidates for Town Meeting

Winchester operates under a representative town meeting system that serves as the town's legislative body. Unlike open town meetings, where all residents can vote, Winchester's system consists of elected representatives who make decisions on town budgets, bylaws and major policies on behalf of their constituents. Out of 351 communities in Massachusetts, only 32 operate under a representative format.

Winchester Town Meeting is composed of 192 members, divided equally among the town's eight precincts. Each precinct elects 24 representatives to ensure balanced representation. Terms are staggered so that one-third of the seats — eight per precinct — are up for election each year, with members serving three-year terms. This system maintains continuity while allowing for consistent renewal of representation.

In this election cycle, 69 town meeting member seats are up for election across Winchester's eight precincts. Each precinct has eight three-year terms available. Additionally, Precinct 2 has one two-year vacancy, Precinct 3 has one one-year vacancy and Precinct 5 has three one-year vacancies.

Town Meeting candidate lists will be published after nomination papers are certified in early February. The League of Women of Voters and Winchester News will send out questionnaires to all candidates running for Town Meeting, and candidate profiles will be published online in late February.

Precinct 1 (eight seats, three-year terms)
Precinct 2 (eight seats, three-year terms; one seat, two-year term)
Precinct 3 (eight seats, three-year terms; one seat, one-year term)
Precinct 4 (eight seats, three-year terms)
Precinct 5 (eight seats, three-year terms; three seats, one-year terms)
Precinct 6 (eight seats, three-year terms)
Precinct 7 (eight seats, three-year terms)
Precinct 8 (eight seats, three-year terms)

Write-in candidate opportunities

Several races on the March 21 ballot have fewer candidates running than seats available. The following offices have write-in opportunities:

— Library Board of Trustees (two seats, three-year terms): One candidate on ballot
— Precinct 2 Town Meeting, two-year term: No candidates on ballot
— Precinct 8 Town Meeting, three-year term (eight seats up for election): Seven candidates on ballot

The town clerk encourages anyone planning to run a write-in campaign to contact their office to register their intent. The League of Women Voters of Winchester and Winchester News will publish candidate profiles for candidates planning a write-in campaign.

The Prop. 2 1/2 override

This election won’t just be about candidates. Winchester voters will also decide on a proposed $11.5 million Proposition 2½ override that would increase the town’s tax levy capacity and affect town and school budgets — and likely property tax bills — over the next several years.

At its Feb. 12 meeting, the Winchester Select Board reached consensus on an override totaling $11.5 million, split into $9 million for operations and $2.5 million for capital stabilization. Operating funds are intended to provide a three- to four-year runway for town and school services. Capital funds would be divided between the building stabilization fund and capital stabilization fund for facilities needs, including Town Hall restoration and school infrastructure.

Based on projections presented during deliberations, the override would raise the average single-family tax bill by about $1,006 in FY2027 and $1,463 in FY2028 (about $122 per month at midpoint estimates), with impacts varying by assessed value.

Board members framed the proposal as a response to structural budget pressures — including school staffing, municipal services and long-term capital needs. Discussion focused on how much of a cushion to seek versus relying on cost controls and projected revenue growth.

As part of the final consensus, the board also voted to create a transfer station working group to boost commercial revenue, cap municipal health insurance expense growth at 12% annually and sponsor a Spring Town Meeting article to replenish the health care stabilization fund using available override revenue.

For full projections, modeling, and supporting materials, visit the town’s State of the Town page.

2026 town election coverage

This collection brings together Winchester News coverage leading up to the March 21 municipal election. It includes reporting on who is running, how to vote, key deadlines and the major policy questions framing the ballot. The page will be updated as new information becomes available, reporting takes place and will remain active through certification of the final results.

Feb. 13 — Winchester Select Board settles on $11.5M override after marathon negotiation

Feb. 13 — 2026 Town Election Guide now live, designed as ongoing civic information hub

Feb. 10 — Winchester Special Town Meeting sharpens override debate as Select Board weighs final price tag

Feb. 6 — Incumbents, newcomers appear on certified list after nomination deadline

Jan. 28 — Select Board debates Winchester property tax override, members split on amount

Jan. 26 — Who has pulled nomination papers so far for 2026 Winchester town election?

Jan. 15 — Winchester Select Board schedules Special Town Meeting on fiscal challenges

Jan. 7 — Winchester school officials seek $4.5M to fund literacy, equity improvements

Dec. 15 — Want to run in Winchester? Nomination papers open Jan. 2 for 2026 town election

Sept. 23 — State of Town Committee charting Winchester override strategy