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Spirit Night 2023

Winchester Center Winchester, MA

Main and Thompson Streets will be closed from 4 pm-9 pm, stores will be open! 5:30 pm:  Live performance by Pogo Fred 6:00 pm Live Music from Winchester's Sounds Like...

Pogo Fred to Perform!

Winchester Center Winchester, MA

Pogo Fred holds multiple Guinness World Records for his extreme pogo stunts and is regarded as one of the best jumpers on the planet. Join us during Spirit Night, Friday...

Spirit Weekend Farmers Market

Town Common Winchester, MA

Market Season runs the 2nd Saturday of June through the last Saturday of October from 9:30am-1:30pm. Come explore and enjoy local food, music, artists, organizations & businesses at our weekly...

Glen Doherty Memorial Road Race

Winchester Town Hall 71 Mt. Vernon Street, Winchester, MA

The Annual Glen Doherty Memorial 5K/10K Road Race is now in its second decade! This is our key fundraising event, and a fun one where everyone can participate - serious runners, casual runners,...

Spirit Weekend Biergarten (aka Beer Garden)

Griffin Museum of Photography 67 Shore Road, Winchester, MA

NEW DATE! Join us on Sunday, Sept 24th from 2:00 - 6:00 pm on the Griffin Museum of Photography's beautiful outdoor patio to enjoy locally crafted beer & cider from...

Midnight Madness is Back!

Get ready for a cherished Winchester tradition that will kickstart your holiday season in the most charming way possible! 🎁🌟 Join us in downtown Winchester for an evening of shopping,...