The Winthrop High School Class of 2027 is raising funds with a community-wide “Paint the Town Blue and Gold” initiative. Residents can display their school pride by ordering a painted “W” stencil for their private driveway or walkway for a donation of $40. Town sidewalks are strictly excluded.
Payment may be completed by cash, check payable to “WHS Class of 2027,” or Venmo (@WHS-Classof2027). Community members can sign up using the online registration form at forms.gle/ dvGGzhNsNCUjxJf96. For inquiries, contact cldemayo@gmail.com.
Winthrop Public Health is holding weekly flu vaccination clinics every Tuesday from 9 a.m. to 6 p.m. at the EB Newton Building, located on the first floor at 45 Pauline Street.
The clinic offers regular flu shots for individuals ages 2 and older, as well as high-dose flu shots tailored for seniors ages 65 and up. Residents may walk in during clinic hours or pre-register in advance. For questions or additional information, call the Public Health Department at 617-539-5844.
The Winthrop Commission on Diversity, Inclusion and Community Relations is sponsoring “Italian Heritage Month: Spotlight on Winthrop” on Saturday, Oct. 24, 2026, from 12 p.m. to 2 p.m. in French Square.
The afternoon program celebrates Italian culture, traditions, and community heritage in Winthrop. The event will feature live music, food, and guest speakers. All residents are invited to attend.
Local families can turn leftover jack-o’-lanterns into garden nourishment at the 6th Annual Great Pumpkin Roll on Saturday, Nov. 7, 2026, from 2 p.m. to 4 p.m. at the Fort Banks School Playground.
The free event is co-sponsored by Mothers Out Front and the Winthrop Department of Public Works to divert seasonal food waste away from trash incinerators and into municipal compost. Participants can roll their pumpkins down the hill for collection. To ensure safe composting, all pumpkins must be free of paint, stickers, plastics, and glitter. The event includes children’s crafts along with complimentary apple cider and treats; attendees are asked to bring their own mugs.
The Town of Winthrop Transfer Station, located at the end of Kennedy Drive before Belle Isle Cemetery, is open for the season through Saturday, Dec. 5, 2026.
Operating hours are:
• Fridays: 9 a.m. to 12 p.m. and 3 p.m. to 6 p.m.
• Saturdays: 9 a.m. to 12 p.m. and 1 p.m. to 3 p.m.
Disposal of leaves and grass clippings is free and restricted strictly to Winthrop residents. Proof of residency must be presented via a valid resident parking sticker, driver’s license, or town ID displaying a current Winthrop address. Commercial properties, commercial vehicles, landscapers, and hired contractors are strictly barred. Town DPW staff will inspect all incoming loads and verify residency at the gate.
Branch disposal is governed by specific regulations:
• Branches exceeding 3 inches in diameter will not be accepted.
• Transporting branch loads requires a Transfer Station Pass, valid only for non-commercial pickup truck loads up to a 5-yard maximum.
• Passes cost $20 and must be purchased in advance at the DPW offices, open Monday through Thursday from 7 a.m. to 3 p.m. Credit cards or checks are accepted; cash is not accepted.
For more details, visit winthropma.gov or contact the DPW at 617-846-1341.
The Town of Winthrop is reminding property owners and residents of municipal ordinances regulating public shade trees, designed to preserve the urban canopy, protect wildlife habitat, safeguard property values, and mitigate climate impacts such as flooding, heat, and erosion.
Residents must apply for and obtain a Tree Work/Removal permit from the Tree Warden prior to:
• Planting any public shade tree
• Conducting construction within the dripline of a public tree
• Pruning any public tree
Under town rules, permits may only be approved if at least one of the following criteria is met:
• The tree is dead, diseased, injured, in imminent danger of falling, disrupting utility lines, or posing an immediate danger to pedestrians or vehicles.
• Trimming or removal is necess
The MBTA has announced the release of five new special edition collectable CharlieCards featuring iconic Boston landmarks including: the Massachusetts State Capital building, Bunker Hill Monument, the Boston Tea Party Ship & Museum, the Old State House, and TD Garden.
The MBTA’s Customer Experience team in partnership with the MBTA Fare Revenue Department previously released three commemorative cards in summer 2026.
“Riding the T is one of those things that makes Boston, Boston,” said Interim Secretary of Transportation and MBTA General Manager Phillip Eng. “I say that myself as someone who is proud to call Boston home. The T is one of the best ways to travel and see all that Massachusetts has to offer, and today we’re excited to reveal a new set of limited edition CharlieCards, which feature iconic Boston landmarks that remind so many people of the amazing city we live in and its rich history.”
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