Winchester Chamber of Commerce and The Glen Doherty Memorial Foundation to host: Spirit Weekend 2026!
The Winchester Chamber of Commerce, in partnership with The Glen Doherty Memorial Foundation, have organized Spirit Weekend 2026 for the weekend of September 18-20th 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! Thank you to Winchester Savings Bank for sponsoring the weekend!
Schedule of Events for Spirit Weekend 2026:
- Friday, September 18th Spirit Night! 4:00 pm-9:00 pm. The streets of downtown Winchester will be closed from 4 pm-9 pm, but stores and restaurants will be open! 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!
Friday, September 18th: Cheer on Varsity Field Hockey and the Girls Varsity Volleyball teams! Field Hockey faces off at 4:15 at Knowlton field, and volleyball serves at 5:30 in the High School Gym
- Saturday, September 19th, 10:00-5:00 pm: Shop local and score big savings during our 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.
- Saturday, September 19th, 9:30-1:00 Community Connects Day at The Winchester Farmers Market. Community Connect Day is your chance to engage with the local organizations that make our town such a vibrant and welcoming place to live.
- Saturday September 19th, 9 AM-1 PM, Winchester Town Hall, Shred It & Share It 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
- Saturday, September 19th, 9-11: am: Steps and Stories Audio Book Walk at Book Ends, 559 Main Street
- Saturday, September 19th, 11:00 am, Story Hour, Book Ends 559 Main Street
- Saturday, September 19th, 3:00 pm-6:00 pm Spirit Weekend Beer Garden! Join your neighbor’s 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 our sponsors, Catherine Albiani Real Estate , and Kate Maloney Interior Design
- Sunday, September 20th Noon, Winchester Town Hall: End the weekend running the Annual Glen Doherty Memorial Race!. 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 Ten years of friends, family, neighbors, runners, walkers, ruckers, locals and visitors honoring our 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!
- Sunday, September 20th: Winchester Sports Foundation’s “Hall of Fame” ceremony, 6 pm Burlington Marriott. Buy Tickets here
Should be a great weekend to support local!
