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The following was submitted by the Winchester Chamber of Commerce:
The Winchester Chamber of Commerce, in partnership with The Glen Doherty Memorial Foundation, have organized Spirit Weekend 2026 for the weekend of Sept. 18-20.
The weekend has now become an annual event where the community comes together to not only honor Winchester’s hometown hero, Glen Doherty, but also to celebrate the unique spirit of Winchester.
The Chamber invites all residents of Winchester and beyond to plan for a great weekend of local shopping, dining and celebrating.
The Chamber wishes to thank Winchester Savings Bank for sponsoring the weekend.
Schedule of Events for Spirit Weekend 2026:
• Sept. 18: Spirit Night – Downtown Winchester, 4-9 pm.
The streets of downtown Winchester will be closed from 4-9 p.m., but stores and restaurants will be open.
There will be live music from Winchester’s own Sounds Like Chicken, a live performance by Kimberly’s Pocket Circus, high school and youth organizations will be selling “Spirit Wear” in booths on the streets and so much more.
• Sept. 18: Varsity games starting at 4:15 p.m.
Cheer on Varsity Field Hockey and the Girls Varsity Volleyball teams. Field hockey faces off at 4:15 p.m. at Knowlton field, and volleyball serves at 5:30 p.m. in the Winchester High School gym.
• Sept. 19: Town Sidewalk Sale – Downtown Winchester, 10 a.m.-5 p.m.
Shop local and score big savings during the Town-Wide Sidewalk Sale. Retailers throughout town will be bringing their best deals and discounts right outside their storefronts — come stroll, shop, and discover something special.
• Sept. 20: Community Connect Day at Winchester Farmers Market, 9:30 a.m.-1:30 p.m.
Community Connects Day is your chance to engage with the local organizations that make our town such a vibrant and welcoming place to live.
Saturday, Sept. 19 Events
• 9 a.m.- 1 p.m.: Shred It & Share It at Winchester Town Hall
Shred It & Share It is brought to you by Andersen Group Realty. A free community event where neighbors can securely shred old documents and donate housewares and bikes to benefit The Mission of Deeds and Bikes Not Bombs.
All the details here.
• 9-11 a.m.: Steps and Stories Audio Book Walk at Book Ends, 559 Main St.
• 11 a.m.: Story Hour at Book Ends, 559 Main St.
• 3-6 p.m.: Spirit Weekend Beer Garden at Griffin Museum Outdoor Patio
Join your neighbors and friends to celebrate the Winchester Spirit on The Griffin Museum of Photography’s beautiful outdoor patio. Live music provided by Kevin Haverty, beer poured by Arlington Brewing Co. and food for sale from Nouvelle Maison.
This is intended as a family friendly event for all to enjoy and is brought to you by The Winchester Cultural District, The Winchester Chamber of Commerce and sponsors Catherine Albiani Real Estate and Kate Maloney Interior Design.
Sunday, Sept. 20 Events
• 9:30-11 a.m.: T-Shirts and merchandise for sale, Jenks Center parking lot, 109 Skillings Road
• 12 p.m.: Annual Glen Doherty Memorial Race at Town Hall
There is plenty of time to register if you have not already. Create a team with neighbors and friends and enjoy this wonderful event.
Over 10 years of friends, family, neighbors, runners, walkers, ruckers, locals and visitors honoring local legend Glen Doherty. This year will be more epic than ever.
Sign up soon to guarantee a great race shirt and a great day.
• 5 p.m.: Winchester Sports Foundation’s “Hall of Fame” Ceremony at Burlington Marriott
Cocktails for the event begin at 5 p.m. followed by the ceremony at 6 p.m.
Buy tickets here.
For a list of specials and discounts offered throughout the weekend, click here.
