John Bellaire, 22, among youngest townwide winners in Winchester history
He won all eight precincts after a door-to-door campaign that emphasized direct voter contact over institutional backing.
2026 Town Elections
13 YEARS OF DATA, ONE SATURDAY: Takeaways from Winchester’s override vote and the races that surrounded it
Winchester News reviewed precinct-level election results from every annual town election since 2014 — 13 years of data covering turnout, ballot questions, Select Board races, School Committee contests and Planning Board results — and compared them against the March 21 preliminary numbers. The 2026 results have not yet been certified by Town
With override rejected, Winchester shifts from campaigning to budget planning
After Winchester voters rejected an $11.5 million Proposition 2 1/2 override on Election Day, March 21, the governing question in town has shifted from persuasion to arithmetic. Select Board member Bill McGonigle, who served on the Yes for Winchester campaign, said the defeat has changed how he approaches
Voters fill Town Meeting seats across Winchester; four incumbents unseated
The biggest shakeup came in Precinct 7, where two officeholders lost in an 11-person contest, matching Precinct 4 for the busiest race.
Winchester’s $11.5M override falls short; Prior returns to Select Board, Bellaire joins School Committee and Beliveau unseats Rossettos
The pattern broke. For seven straight votes stretching back to 2017, Winchester voters had said yes to every Proposition 2½ question put before them — school buildings, operating budgets, capital needs. The Lynch Elementary School project passed in 2023 with 82.4% support, the highest for any school ballot question in
For years, Winchester voters rejected nearly every tax override. Then the pattern flipped.
Editor’s note: An interactive visualization of all 33 Proposition 2½ ballot questions in Winchester from 1988 through 2023, including results by decade, override type and individual vote, is available here. From November 1988 through January 2023, Winchester voters went to the polls 25 times to decide 33 Proposition 2½
Process, pace set Prior and Brady apart in Winchester Select Board race
The contest highlights competing governing styles, one emphasizing consensus and process, the other urging faster action and visible dissent.
Select Board candidates align on override, diverge on how to grow Winchester’s bottom line
Ahead of the March 21 election, incumbent Michelle Prior and challenger Shamus Brady offered contrasting styles, but frequent agreement at a candidate forum for the Select Board, with both backing the pending override vote while differing on how to generate revenue, speed housing development and attract businesses. The two are
School Committee candidates call for teacher reviews, clearer goals at Winchester forum
John Bellaire and Heather von Mering outlined competing visions for the town’s public schools at a candidate forum, clashing over technology in classrooms, special education access and teacher accountability ahead of the March 21 election. The two are vying for one three-year seat on the Winchester School Committee. The
Winchester School Committee candidates bring contrasting backgrounds to Thursday forum
Two candidates for Winchester’s School Committee will face voters at a forum as the district navigates a new literacy curriculum, budget pressures and questions about student mental health. Heather von Mering and John Bellaire are competing for an open seat on the School Committee, which oversees a budget von
Winchester Town Clerk: Early voting begins March 14
The following was submitted by the Winchester Town Clerk’s Office: Did you know that you can cast a vote early for the upcoming Annual Town Election? Election laws were amended years ago and allow for voters to cast ballots several ways. The world is a busy place with family,
Winchester seeks poll workers for 2026 election season
The Town Clerk’s Office is seeking workers for the upcoming 2026 election season to assist staff with election administration. Officials cited changes in many election laws in the recent Voter Act of 2022 as a reason for the variety of available positions. The town is looking for serious applicants
Winchester Planning Board candidates debate housing growth and historic preservation
Three candidates for two open seats on the Winchester Planning Board debated housing production, zoning reform and growth Feb. 26 at a forum sponsored by the League of Women Voters of Winchester. Incumbents Nicholas Rossettos and Keri Layton were joined by challenger Amy Beliveau at the Jenks Center, moderated by
Candidate profiles now available in 2026 election guide
Candidate profiles for both the town wide and Town Meeting member races are now live in the Winchester News/League of Women Voters of Winchester 2026 Election Guide. While the deadline for submission was Feb. 24, if a candidate has not turned in their profile and/or headshot, they may
Michelle Bergstrom steps away from Winchester School Committee to focus on full-time teaching
Michelle Bergstrom, a nine-year member of the Winchester School Committee, announced she will not seek re-election, citing her return to full-time elementary classroom teaching as the reason for stepping down. “At my core, I am an educator. I have returned full time to the elementary classroom, a decision that feels
League of Women Voters looking for resident questions for candidate forums
The following was submitted by the League of Women Voters of Winchester: The League of Women Voters of Winchester will hold candidate forums at the Jenks Center Cummings Room for all town wide offices with more candidates than open seats. Planning Board – Feb. 26 at 6:30 p.m. Amy