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. Voters should bring a valid form of identification, though it is not required under Massachusetts law. Acceptable forms include a driver's license, state ID, passport, employee ID, student ID or utility bill with name and address.

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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:

Date	Action
Feb. 2	List of candidates who submitted nomination papers published
Feb. 27	Deadline for candidates to submit profile information
Early March	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
— Jason Roeder

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.

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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 early March.

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)

How to get on the ballot

Nomination papers became available Jan. 2 at the town clerk's office in Town Hall, 71 Mt. Vernon St. Papers must be obtained by Jan. 28 and returned with sufficient signatures by noon Jan. 30. Signature requirements:
— Townwide office candidates need 50 signatures from registered Winchester voters.
— Town meeting candidates need 10 signatures from registered voters in their precinct.
— Incumbent town meeting members can get on the ballot by notifying the clerk in writing by Feb. 13.

Debates and forums

The League of Women Voters of Winchester is working to organize debates for candidates in contested Town-wide elections and forums for Town Meeting candidates to meet voters. The debates and candidate forum events have been tentatively scheduled for March 5 and 12, and will be finalized based on candidate availability and WinCam scheduling. Information about dates, times and participating candidates will be published as it becomes available. Links to video recordings of candidate debates will be posted here once available from WinCam