The Winchester News 2025 election guide

This guide is designed to inform Winchester voters and encourage civic participation. Stay engaged, ask questions and make your voice heard in the March 22 municipal election. Feel free to return to this space as it will serve as a living resource for voters, providing details on candidates, voting logistics, upcoming forums and election results.

Election Day details

The Winchester municipal election will take place on March 22, with polling open from 7 a.m. to 8 p.m. at Winchester High School cafeteria, 80 Skillings Road, which will serve as the central polling location for all eight precincts due to ongoing construction in the gymnasium. The last day to register to vote is March 12, and the deadline to request a vote-by-mail ballot is March 17.

Townwide candidates

Eleven townwide offices across eight key areas of Winchester's municipal government are up for election. This year's contest marks a significant transition in town leadership, with six incumbents choosing not to seek reelection, five current officeholders seeking to retain their seats and six newcomers vying for elected positions.

The Winchester News has sent detailed questionnaires to all candidates running for townwide offices, asking about their backgrounds, qualifications and positions on key issues facing Winchester. Click on a candidate's name below to read their biographical information and positions on key issues facing Winchester.

Contested races
Select Board (two seats, three-year terms)
— Anthea Brady (incumbent)
— Dorothy Simboli
— Richard Welch Jr.
— Paras Bhayani

School Committee (two seats, three-year terms)
— Karen Maruyama Bolognese (incumbent)
— Christian Nixon (incumbent)
— Stefanie Mnayarji

Uncontested races
Town moderator (one seat, one-year term)
— Philip Frattaroli (Heather von Mering not seeking reelection after five terms)

Board of Assessors (one seat, three-year term)
— George Nowell Jr. (incumbent)

Board of Health (one seat, three-year term)
— Anne Marie Hill (Ruth Trimachi stepping down)

Library Board of Trustees (two seats, three-year terms)
— David Coughlan (incumbent) seeking one of two available seats

Positions without candidates
— Housing Authority commissioner (four-year term)
— Library trustee (one three-year seat, being vacated by Wendy Karle)
— Planning Board (three-year term, being vacated by Diab Jerius)

Town Meeting representative candidates

Winchester operates under a representative town meeting system, a mini-republic 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, 64 town meeting member seats are up for election across Winchester's eight precincts, with eight three-year terms available in each. There is a one-year term, Precinct 5 - 1 for a two-year term.

Town Meeting candidates have also received questionnaires focused on their views about local governance and their priorities for their respective neighborhoods. To read their respsonses, visit: https://bit.ly/4i0elYw

How to vote

Voting status: Residents can register to vote, update their address and check their voter registration status through the state's online voter registration system. The portal is accessible at bit.ly/4jCAJZH

By mail: Residents can request a vote-by-mail ballot until March 17. Ballots must be completed and returned by election day, March 22, at 8 p.m. Access a vote-by-mail application: bit.ly/41kmAsU

Absentee: Absentee voting is available for registered Winchester voters who will be away on election day or are unable to vote in person due to disability or religious beliefs. Applications for absentee ballots must be submitted by March 18. Voters can obtain applications from the town clerk's office or online. Completed ballots must be returned by 8 p.m. on March 22, to be counted. More information here: bit.ly/410KJDI

Early in-person early voting: Voters who wish to cast their ballots ahead of Election Day can take advantage of early in-person voting at Town Hall, Winchester Room, first floor. Below is the schedule for early voting:

Election Day voting: Voting will take place in the Winchester High School cafeteria rather than the gymnasium due to an ongoing construction project. The cafeteria is located at 80 Skillings Road and will serve as the central polling location for all eight precincts. The voting hours remain the same — polls will be open from 7 a.m. to 8 p.m. on March 22.

Election coverage and candidate forums

The Winchester News is partnering with WinCam and the Winchester League of Women Voters to provide comprehensive coverage of the March 22 town election, including candidate forums, video coverage and detailed candidate profiles.

The Winchester League of Women Voters will host candidate forums for the two contested races at the Cummings room of the Jenks Center, 109 Skillings Road.

Residents can submit questions for either forum through Feb. 25 by emailing candidatequestions@lwvwinchester.org. The League of Women Voters will select questions based on their relevance, fairness and potential to generate informative responses from the candidates.

Meanwhile, the Winchester League of Women Voters will publish an online voters' guide with submissions from candidates, including those running unopposed and town meeting candidates (The Winchester News will add a link to their guide when it's published).

WinCam will provide live coverage of the League of Women Voters candidate forums and make the recordings available on-demand. Winchester News will embed these forum videos directly into our comprehensive candidate guide following their publication.

Meet and mingle event
For a more casual setting, candidates will also participate in a planned "meet and mingle" event, sponsored by the the Winchester Chamber of Commerce, the Network for Social Justice and the Town Common Task Force, on Tuesday, March 11, from 5:30-7:30 p.m. at Kyuramen Restaurant, 538 Main St. Complimentary appetizers will be provided, and a cash bar will be available. The event is open to all candidates. Addmission is free, though registration is required due to space limitations: bit.ly/4hEpWNm

Helpful links