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Oct. 17, 2026
October 17, 2026

Winchester boys soccer rattles off three straight wins to secure 10th seed in Division 1 with four games left in regular season

Oct. 16, 2026
October 16, 2026

Winchester’s Ambrose PTO dons traffic cone costumes to promote safe school drop-off

Oct. 16, 2026
October 16, 2026

Despite second straight loss, Winchester football still in control of its playoff fate

Oct. 15, 2026
October 15, 2026

TMMA Bulletin - October 14, 2026

Oct. 15, 2026
October 15, 2026

Winchester High School’s Farmers Market Club takes leadership role in community

Oct. 14, 2026
October 14, 2026

The nine Massachusetts ballot questions, explained

Oct. 14, 2026
October 14, 2026

What can AI do for me? The Wilson Science & Technology Forum has some ideas

Oct. 14, 2026
October 14, 2026

St. Eulalia’s Church presents ‘Voices for Ukraine’ benefit concert

Oct. 14, 2026
October 14, 2026

Winchester girls volleyball climbs D-1 power rankings after beating Oliver Ames in classic non-league showdown

Oct. 14, 2026
October 14, 2026

WIN Fast Forest celebrates birthday, WHS students help out and Forest Ridge petition available to sign

Oct. 14, 2026
October 14, 2026

Winchester Historical Society welcomes two new directors for education, communications

Oct. 14, 2026
October 14, 2026

Winchester looks at possible new budget manager position

Oct. 13, 2026
October 13, 2026

31st Middlesex District Candidates Forum to be held Oct. 15

Oct. 13, 2026
October 13, 2026

Winchester student-led Tree Preservation Project launches community survey

Oct. 13, 2026
October 13, 2026

Winchester offers residents several ways to register to vote

Oct. 13, 2026
October 13, 2026

Winchester Explained: Historical Commission preserves, protects town’s legacy and future

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