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
The Select Board voted Dec. 22 to offer the position of town manager to Christopher Senior, following a prolonged debate over contract length and performance evaluation timelines that exposed divisions among members about the collapsed search process. The board ultimately approved a two-year contract for the former Cohasset town manager
Winchester’s search for a permanent town manager will face a pivotal decision Dec. 22 after two of three finalists withdrew from consideration, leaving Christopher Senior, former town manager in Cohasset, as the sole remaining candidate and prompting the Select Board to weigh whether to reset the process entirely. Senior,
Deliberations Monday will determine whether to proceed forward or restart efforts after unexpected departures narrowed the field to one.
Finalist Eric Duffy has withdrawn from Winchester’s search for a permanent town manager, Select Board member Mike Bettencourt said Wednesday, as residents raised questions about two finalists’ backgrounds and the town’s vetting process ahead of scheduled public interviews and community events. Select Board Chair Michelle Prior declined to
Winchester residents have multiple opportunities this week to meet, observe and learn about the three finalists competing to become the town’s next town manager, Select Board member Anthea Brady announced on Monday. The schedule includes formal Select Board interviews, a less formal community session where residents can ask questions
Interim Town Manager Stephen Delaney will leave his post earlier than expected for personal reasons, the Select Board announced at its Dec. 15 meeting, departing as Winchester prepares for a potential override vote in the tens of millions and searches for a permanent hire. Delaney, who began serving as interim
Winchester’s annual town election will take place March 21, giving voters the opportunity to select officeholders for positions that guide municipal policy, oversee town departments and manage the budget. The annual town election will put races for town moderator, the Select Board, the School Committee and a range of
The Select Board will interview three finalists for town manager during the week of Dec. 15, marking a pivotal step in a search that began after Beth Rudolph’s unexpected resignation in July and comes as Winchester confronts significant fiscal pressures and major infrastructure needs. The candidates are Joseph Domelowicz
The Winchester Historical Society marked the town’s 175th anniversary with the world premiere of “The Changing Shape of Winchester,” a documentary examining how the community’s boundaries evolved since its 1850 incorporation. Filmmaker Peter Engeldrum presented his latest work to a full house at the Jenks Center, concluding a
The Select Board on Nov. 17 voted to keep a single property tax rate for fiscal 2026, continuing Winchester’s long-standing practice of taxing homes and businesses at the same rate. According to the town’s tax classification memo, the overall FY26 rate will be $10.56 per $1,000,
Town Meeting members voted to indefinitely postpone a proposal for the town to purchase 13.4 acres off Forest Circle for conservation purposes during the final night of their fall session Nov. 10, ending a three-night gathering that also saw approval of affordable housing funding and multiple labor contracts. Article
Members rejected an immediate shift in parliamentary procedure, opting instead for more study before replacing Robert’s Rules.
Winchester Town Meeting members approved $4.4 million in capital appropriations Monday night while receiving sobering warnings about a looming structural deficit and hearing updates on the town’s newly secured climate leader status and ongoing search for a permanent town manager. The opening session of Winchester’s Fall 2025
The Winchester Select Board recently voted to appoint Murphy, Hesse, Toomey & Lehane LLP as the town’s new legal counsel, concluding a monthlong search that drew three finalists and extensive board deliberation. The Quincy-based firm began its work ahead of Fall Town Meeting. Board members cited the firm’s
Officials outlined a multiyear plan to stabilize funding through updated fees, long-term liability planning and potential new revenue streams.
