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Winchester residents to get two chances to weigh in on override, Forest Ridge debates

Select Board Chair Anthea Brady said the survey is intended to inform “how we message the need,” what type of information the town distributes and how the board approaches the process. WINCHESTER NEWS STAFF PHOTO / PETER CASEY

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Winchester residents who still have something to say about the failed override or the town’s possible purchase of Forest Ridge will have two chances this week to put questions before town officials.

The Select Board will hold an online focus group on Zoom at 8 p.m. Tuesday, June 23, on the $11.5 million override voters rejected in March.

The Conservation Commission will hold a Forest Ridge land acquisition forum online via Zoom at 7 p.m. Wednesday, June 24, in the Winchester Room at Town Hall, 71 Mt. Vernon St., with a remote option through Microsoft Teams.

The meetings are separate. Together, they return residents to two unresolved spring decisions: how the town should respond after a large Proposition 2½ request failed at the ballot box, and whether Winchester should keep pursuing conservation ownership of one of its remaining large undeveloped parcels.

The Select Board session is billed as a focus group meeting under the title “Let’s discuss the override.” A town notice says the board “wants to hear from you.” The meeting will be held on Zoom, and a town flyer also directs residents to an online survey through a QR code and link.

The March 21 ballot question failed by 293 votes, 2,558-2,265. It would have raised $11.5 million, including $9 million for town and school operations and $2.5 million for capital stabilization. Town officials have said the override was meant to help close a roughly $5 million structural deficit and address capital needs.

The board held an in-person listening session June 17 in the Select Board Room. The Tuesday meeting gives residents another forum as the board considers whether to return to voters with another override proposal and, if so, how to structure it.

The survey asks what factors shaped residents’ votes, what additional information would have helped them decide and whether they prefer one combined ballot question or separate questions for operating and capital needs.

Conservation Commission Chair Tracy Olson makes the case in support of the town purchasing the 13-acre Forest Ridge property during Town Meeting. WINCHESTER NEWS/WINCAM PHOTO/CHRIS STEVENS

The Forest Ridge meeting the next night turns to a land acquisition proposal that failed at Spring Town Meeting but has not disappeared from the town calendar.

The Conservation Commission has described the Wednesday session as an information discussion and open forum on the acquisition project. A flyer says the public is welcome and encouraged to bring questions and concerns.

At Spring Town Meeting, Article 35 would have authorized the Conservation Commission to acquire about 13.66 acres near Forest Circle in Winchester and Fallon Road in Stoneham for conservation and passive recreation and borrow up to $3 million for the purchase.

Town Meeting defeated the motion 59-105, and a related $28,500 transfer for one-time legal and acquisition costs had no action taken.

Supporters have framed Forest Ridge as a chance to preserve open space, protect wildlife habitat, maintain tree canopy, reduce stormwater impacts and create passive recreation opportunities.

The Conservation Commission’s Community Preservation Act application said the land abuts the Middlesex Fells Reservation and could become the only town-owned conservation land on the east side of Winchester.

The application put the possible purchase price between $3 million and $3.6 million, depending on negotiations with the landowner and grant reimbursements. It identified the owner as Shannon Investment Trust and said no purchase agreement had been reached at the time.

The posted agenda for Wednesday does not list a vote. It calls for a Forest Ridge discussion and says the session will be an information discussion about the acquisition project.

For residents, the back-to-back meetings offer two different conversations: one about how much money the town should ask taxpayers to raise, and another about whether Winchester should spend Community Preservation Act-backed money to buy land before future development pressure returns.

The override focus group will be online at 8 p.m. Tuesday. The Forest Ridge session will begin at 7 p.m. Wednesday at Town Hall and online through Microsoft Teams.

Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He is also the founder and editor of The Marblehead Independent, a reader-funded digital newsroom.

Winchester News is a non-profit organization supported by our community. If you appreciate having local Winchester news, please donate to support our work, and subscribe to our free weekly newsletter. Copyright 2026 Winchester News Group, Inc. Copying and sharing with written permission only.

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