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Spirit Weekend returned to Winchester for its sixth year with new events, activities

Winchester residents enjoy visiting the Farmers Market on Saturday, Sept. 19 during the Community Connects Day event, which was part of the sixth annual Spirit Weekend. WINCHESTER NEWS STAFF PHOTO/TAVISHI CHATTOPADHYAY

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Spirit Weekend marked its sixth year over the weekend. The annual event runs in conjunction with the Glen Doherty Memorial Foundation, which occurred Sept. 20.

The Glen Doherty Memorial Race honors Glen A. Doherty, a former Navy SEAL and Winchester resident who died in an attack on the U.S. consulate in Benghazi, Libya on Sept. 12, 2012. This was the 10th year the race was held.

Hosted by the Winchester Chamber of Commerce, the 2026 Spirit Weekend kicked off on Friday, Sept. 18 with Spirit Night in downtown Winchester, featuring a variety of activities for families and local businesses which stayed open beyond their regular closing time.

Joe Ficociello and his mom Erin carry a flag during the annual Glen Doherty Memorial Race on Sunday, Sept. 20 outside Winchester Town Hall. They carried the flag for her dad, Lawrence Kelly, who served 30 years in the Navy. WINCHESTER NEWS STAFF PHOTO/NICOLE GOODHUE BOYD

The weekend continued with activities throughout Saturday, Sept. 19 and into Sunday, Sept. 20, including high school varsity sport games, a beer garden at the Griffin Museum of Photography, Community Connects Day at the Winchester Farmers Market, the road race and events at Book Ends.

Dana Garmey, the chamber’s executive director, said the idea for Spirit Weekend came from a Winchester Chamber of Commerce board member who recommended having a community event hosted alongside the race.

It was a way to get business involved in celebrating both Doherty and the spirit of Winchester, said Garmey.

“It’s wonderful for the community to come out and support a wonderful individual,” said Jen Greene, a former Winchester resident attending the Community Connect Day at the Farmers Market.

Rebecca Slisz, the executive director of the Network for Social Justice, which had been tabling during Spirit Weekend, attended the field hockey game on Sept. 18.

It was one of two games that day. The other was a girls varsity volleyball game.

“I was glad to see that the sporting events highlighted two sports for women,” Slisz said.

Garmey said new activities and events have been added over the years. This year, the chamber added the Sidewalk Sale and the Shred It and Share It event, where residents brought old documents to shred and bikes and housewares to donate during Saturday’s schedule.

Attendees at the Winchester Farmers Market speak with local organizations during Spirit Weekend. WINCHESTER NEWS STAFF PHOTO/TAVISHI CHATTOPADHYAY

Sept. 19 also included Community Connects Day, which combined the Farmers Market and local organizations ranging from the Network for Social Justice to the Winchester Cultural Council to the Council of Social Concern and even Winchester News.

The market itself has been a staple for the Winchester community for years and is a “crossroads” between community building and the arts.

Greene has been coming to the Farmer’s Market almost every Saturday to get fresh flowers since she moved to Winchester 14 years ago. She recently just moved, but intends to keep coming back.

“It’s one of my favorite parts about Winchester,” Greene said.

The three-day Spirit Weekend wrapped up on Sunday evening, with the Winchester Sports Foundation’s Hall of Fame ceremony at the Burlington Marriott.

Tavishi Chattopadhyay is a journalism student at Boston University.

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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