Winchester Chamber of Commerce and The Glen Doherty Memorial Foundation to host:  Spirit Weekend 2025!

  • For a list of specials and discounts offered throughout the weekend, click here

The Winchester Chamber of Commerce, in partnership with The Glen Doherty Memorial Foundation, have organized Spirit Weekend 2025 for the weekend of September 19-21st.  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 2025:

  • Friday, September 19th 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! 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!    
  • Saturday, September 20th, 9:00 am:  Histoury Architectural Tour of Winchester brought to you by the Winchester Historical Society.  Tickets can be purchased at Histoury.org
  • Saturday, September 20th, 9:30-1:30 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. Cultural, sports, and service groups, government agencies, faith communities, and more, will have representatives there happy to explain what they do. 
  • Saturday, September 2oth, 11:  am:  Story Hour at Book Ends, 559 Main Street
  • Saturday, September 2oth, 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 Sounds like Chicken and beer poured by Arlington Brewing Co. 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 , Conquer Ninja Gyms Woburn and Kate Maloney Interior Design
  • Sunday, September 21st:  11:00 am-2 pm:  Bottomless Brunch Watch Party at ATavola, 34 Church Street.  Great way to support the cause without having to actually run!
  • Sunday, September 21st:  10:30 am-12:00 pm  Coming out for the race and/or brunch at Atavola?Let your kids share in Spirit Weekend by joining our artist Dani for a fun, spirit themed paint party at Studio on the Common.  $35/child, Ages 5-8.  Sign up here!
  • Sunday, September 21st 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.  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 21stWinchester Sports Foundation’s “Hall of Fame” ceremony, 6 pm  Burlington Marriott.

Should be a great weekend to support local!