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The following was submitted by the Winchester Chamber of Commerce:
It’s Spirit Weekend! From Friday, Sept. 19 to Sunday, Sept. 21, the Winchester Chamber of Commerce will be celebrating the community. Check out the many events happening throughout the weekend:
In the days leading up to Spirit Weekend, 5,000 flags will be put out marking the route of the Glen Doherty Memorial Road Race.
The road race is in memory of Doherty, who grew up in Winchester and was one of four Americans killed in a terror attack at the U.S. Consulate in Benghazi, Libya. Read his story at glendohertyfoundation.org.
Friday, Sept. 19
Spirit Night! 4 p.m.-9 p.m. The streets of downtown Winchester close, but stores and restaurants will be open! There will be live Music from Winchester’s own Sounds Like Chicken and a performance by Pogo Fred and high school and youth organizations will be selling “Spirit Wear” in booths — plus so much more.
5-9 p.m.: “Spirit Wear” on sale at the corner of Main Street and Thompson Street
5:15 p.m.: Winchester High School Football Team marches through town
5:30 p.m.: Performance by Pogo Fred on Main Street
6-9 p.m.: Live music by Sounds Like Chicken on Main Street
6:30 p.m.: “Friday Night Lights” kickoff at Knowlton Stadium, WHS Varsity Football vs. Waltham High School
Saturday, Sept. 20
Histoury Architectural Tour of Winchester: Brought to you by the Winchester Historical Society. Tickets can be purchased at Histoury.org.
Community Connects Day at the Farmers Market: 9:30 a.m. - 1:30 p.m. “Community Connect Day is a chance to engage with the local organizations that make our town such a vibrant and welcoming place to live,” said Garmey.
Cultural, sports, and service groups, government agencies, faith communities, and more, will have representatives there happy to explain what they do. And Scones by Isobel will be donating all proceeds to Anna’s Fund.
Story Hour at Book Ends, 559 Main St., 11 a.m., featuring Josh Funk and Jen Morris
Spirit Weekend Beer Garden: 3 p.m. - 6 p.m. on the Griffin Museum of Photography’s outdoor patio. Live music will be provided by Sounds like Chicken and beer poured by Arlington Brewing Co. This is listed as a family friendly event for all to enjoy.
Other events:
10 a.m.: Unveiling for “Away” at Town Hall
10:30 a.m.: Riverwalk Tour, begins at Jenks Center
12-2 p.m.: Bib pick-up for Glen Doherty Road Race at Town Hall
Sunday Sept. 21
Bottomless Brunch Watch Party at A Tavola, 34 Church St., 11 a.m.-3 p.m.: Great way to support the cause without having to actually run!
Winchester Sports Foundation’s “Hall of Fame” ceremony, 6 p.m., Burlington Marriott.
Other events
12 p.m.: 12th Annual Glen Doherty 5K/10K Road Race starts at Town Hall
6 p.m.: Winchester Sports Foundation’s “Hall of Fame” Ceremony
Residents can shop and dine locally all weekend long!
For more information, visit 2025 Spirit Weekend – Winchester Chamber of Commerce.
