It’s official! The Charlestown Holiday Festival, previously titled Holiday Stroll, will take place on Sunday, December 15th at the Training Field. From 11 a.m. – 3 p.m. the neighborhood will gather to support local vendors and small businesses, while enjoying a petting zoo, face painting, carolers, hot chocolate, a Santa sighting, and more!
It’s encouraged to continue your afternoon by shopping at all of Charlestown’s lovely local businesses.
This celebration is a long-held Charlestown tradition that was previously canceled due to it’s captain, All Roads Charlestown, having to focus efforts towards the 250th Anniversary of the Battle of Bunker Hill. With your help and additional sponsors, the fun will return!
For more of this year’s Holiday Happenings in Charlestown, check out our full round up!

Abbey is the face behind Caught in Charlestown. In 2023 she migrated from Southie to Charlestown and brought the spirit of the ‘Caught In’ community with her. She is a new momma, creator, real estate agent, yogi, and so much more.
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