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Daily brief · Winchester, MA

Retire by June 2027 to keep Medicare benefit

August 26, 2026

Top story

Winchester approves policy setting retirement deadline for Medicare benefit

Under a policy the Select Board approved Aug. 24, town employees must retire by June 30, 2027, to remain eligible for Winchester's Medicare Part B premium reimbursement in retirement. Roughly 88 employees are eligible to step away. The town has no estimate of how many will go, or of what unused vacation payouts could do to the spring budget.

Winchester News

Sen. Jason Lewis endorses Lipper-Garabedian for state Senate

State Sen. Jason Lewis has endorsed State Rep. Kate Lipper-Garabedian in the Sept. 1 Democratic primary for the 5th Middlesex Senate seat, which includes parts of Winchester.

Winchester News

Capital Planning Committee meets Wednesday evening

The Winchester Capital Planning Committee meets Wednesday, Aug. 26, from 7:30 to 9 p.m. in the Mystic Valley Room at Town Hall.

Town of Winchester

Select Board reviews Town Manager evaluation and contract extension

At its Aug. 24 meeting, the Winchester Select Board reviewed Town Manager Christopher Senior's annual performance evaluation and discussed extending his contract through Dec. 31, 2027.

Town of Winchester

Conservation Commission seeks to acquire Forest Ridge property

An Aug. 24 update to the Select Board detailed the Conservation Commission's proposal to acquire 13.7 acres of Forest Ridge land abutting the Middlesex Fells for conservation and passive recreation.

Town of Winchester

Griffin Museum hosts Ashima Yadava talk

The Griffin Museum of Photography hosts an online Vision(ary) Talks program with photographer Ashima Yadava Wednesday, Aug. 26, from 7 to 8:30 p.m.

FindIt Winchester

Library hosts Game Time for K-2 students

Winchester Public Library hosts Game Time Wednesday, Aug. 26, from 2:30 to 4:30 p.m., with card and board games for rising K-2 students and their families.

Winchester Public Library

Clean Water Action endorses Christine Barber for state Senate

Clean Water Action announced Tuesday, Aug. 25, its endorsement of Rep. Christine Barber in the Democratic primary for the 2nd Middlesex District State Senate seat.

Winchester News

Winchester Cultural Council to host reception for artist Lucia Rubini

The public can meet painter Lucia Rubini and view her work, along with pieces by her students, at a reception at Rubini Art studio Thursday, Aug. 27, from 6 to 8 p.m.

Winchester Cultural Council

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