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When else can you see Pogo Fred, hear Sounds Like Chicken and play an informal game of pickle ball on the streets of downtown Winchester?
It must be Spirit Weekend.
Coming up Sept. 19-21, Spirit Weekend is a time for the community to come together not only to honor hometown hero Glen Doherty, but to also celebrate “the unique spirit of Winchester,” said Chamber of Commerce Director Dana Garmey.
Like playing pickle ball downtown.
Spirit Weekend kicks off with Spirit Night Friday, Sept. 19, from 4- 9 p.m.
“Main Street and Thompson are closed down,” Garmey said. “Pogo Fred will perform, he’s a local business owner, there will be a band, Sounds Like Chicken and we’ll try and do some informal pickle ball – just going to throw up some nets and let people have some fun.”
The pickle ball is new this year, but is a reflection of how the event has changed and grown over the last five years.
“We add a little bit every year because it’s such a fun weekend,” Garmey said.
Along with pickle ball, the Historical Society house tours are also new.
The “Histoury” Tour will take place Saturday, Sept. 20. Garmey said it’s a bus tour of 19th Century homes in celebration of the town’s 175th anniversary.
There are two time slots, 9 a.m. and 1 a.m. For tickets, visit histoury.org and enter WHS in the Donation Code.
Also Saturday is Community Connects at the Farmers Market and the beer garden at the Griffin Museum. Garmey has her fingers crossed for good weather.
Last year’s beer garden, which is always a favorite, Garmey said, was a wash out when a rain storm that was supposed to subside turned into a monsoon.
“They said it would get better, but it just got worse and worse,” she said. “So we’re really hoping for no rain this year.”
The weekend will round out with the road race and the Winchester Sports Foundation’s Hall of Fame dinner on Sunday, Garmey said.
The road race is in memory of Glen 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.
Also leading up to the weekend, Garmey said a number of local businesses will offer specials and discounts to the runners. For a full list go to 2025 Spirit Weekend – Winchester Chamber of Commerce.
And check out below for a full list of weekend events:
Events at a Glance
Flags: 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.
Friday, Sept. 19, 2025
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, said Garmey.
Saturday, Sept. 20, 2025
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.
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.
Sunday Sept. 21, 2025
Bottomless Brunch Watch Party at A Tavola, 34 Church St.: Great way to support the cause without having to actually run!
The Glen Doherty Memorial Race: Town Hall.
Garmey said there is still plenty of time to register, and create a team with family, neighbors and or friends. It has been 10 years of friends, family, neighbors, runners, walkers, ruckers, locals and visitors honoring the local legend and “this year will be more epic than ever,” Garmey said. Sign up soon to guarantee a race shirt.
Winchester Sports Foundation’s “Hall of Fame” ceremony, 6 p.m. Burlington Marriott. For more information, visit the Winchester Sports Foundation.
“It’s going to be a good weekend,” Garmey added. “It’s always such a fun weekend.”
