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Winchester roundup: volunteer openings, recovery coaches, Wiffy fundraiser and summer events

May 29, 2026 | Winchester, Middlesex County, Massachusetts


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Winchester roundup: volunteer openings, recovery coaches, Wiffy fundraiser and summer events
The Winchester Beat hosts covered a range of community announcements, from volunteer recruitment to health and summer events.

Volunteer openings: The Capital Planning Committee seeks one volunteer for a term ending Jan. 1, 2027; the Affordable Housing Trust seeks two volunteers (terms ending April 2028 and April 2029). Applications for those seats are due June 10. The newly formed Transfer Station Data and Resource Committee is seeking five volunteers for terms ending June 30, 2027; applications for that committee were reported due June 8. Hosts directed prospective applicants to the Winchester Committee volunteer application on the town website.

Youth and fundraising: A group of eighth-grade students created a website to help teens find volunteer opportunities; the hosts said the link is available on Winchester News. Wiffy announced a teacher-tribute Flamingo campaign to raise $100,000 to support professional development for Winchester educators. Flamingo tributes start at $25 and can be purchased via Wiffy’s events page (www.wf.org).

Health and social services: The Winchester Health Department is running a recovery program funded from the town’s opioid settlement and has hired two recovery coaches who collaborate with the Winchester Police Department, the Board of Health, schools and the Winchester Coalition for a Safer Community. The Jenk Center’s Winchester Caregivers Network, a Council on Aging initiative, meets in person and virtually and maintains a private Facebook group; membership is open to nonresidents.

Sports and events: Winchester High softball clinched a postseason berth and will play Newton South at home May 29 at 5 p.m.; the high school baseball team also qualified for postseason play. Upcoming community events the hosts listed include the high school Promenade (June 2), graduation at Nolton Stadium (June 5 at 6:00 p.m., weather permitting), Town Day and the Wiffy Road Race (June 6, registration $40), and Porchfest (June 13, register by May 31). The hosts also noted the MBTA will run free commuter-rail service on Fridays in June, July and August and monthly passes are discounted 50% during the same period; monthly passholders may bring a friend for $1 on weekends, subject to MBTA exclusions.

The hosts closed by reminding listeners the show will be on hiatus after this episode and inviting feedback by email and at the Winchester News booth at Town Day.

Why this matters: The announcements affect volunteer recruitment, services for residents dealing with substance use and caregiving, local fundraising for schools, and community engagement opportunities for the summer.

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