BOSTON — Thursday, November 20, 2025 — Today, Mayor Michelle Wu and the Mayor's Office of Tourism, Sports and Entertainment announced the dates for the 29th Annual Enchanted Trolley Tour. This year's Trolley Tour will visit 16 neighborhoods on Saturday, December 6 and Sunday, December 7.
“The annual Enchanted Trolley Tour is a beloved annual tradition bringing families together across the city to kick off the holiday season. I can’t wait to see everyone at this year’s celebrations,” said Mayor Michelle Wu. “I’m grateful for the support of all our partners who help carry out this joyful weekend each year.”
The Mayor's Enchanted Trolley Tour will continue the festive tradition of holiday tree lighting and Santa visits throughout Boston’s neighborhoods. This event is presented by Bank of America, and supported by CityView Trolley Tours. The Enchanted Trolley Tour stops feature giveaways and visits from Santa, Mayor Wu, and Office of Neighborhood Services staff.
"The Enchanted Trolley Tour ushers in the holiday season in a way that only could happen in Boston, charming and delighting residents and visitors throughout a magical weekend," said Miceal Chamberlain, President, Bank of America Massachusetts. "Bank of America is proud to once again join Mayor Wu and the City of Boston in bringing the 2025 Enchanted Trolley Tour and tree lightings to neighborhoods across the entire city."
Enchanted Trolley Tour dates, times, and locations are as follows:
Saturday, December 6 - 11:00 a.m. — Hastings Lot, West Roxbury
- 12:00 p.m. — Wolcott Square, Readville
- 1:00 p.m. — Mattapan Square
- 2:00 p.m. — Hyde Square, Jamaica Plain
- 3:00 p.m. — J.P. Monument, Jamaica Plain
- 3:45 p.m. — Brigham Circle, Mission Hill
- 4:30 p.m. — Bolling Building, Roxbury
- 5:45 p.m. — Blackstone Square, South End
- 6:45 p.m. — Oak Square, Brighton
Sunday, December 7 - 12:00 p.m. — Codman Square, Dorchester
- 1:00 p.m. — Adams Corner, Dorchester
- 2:00 p.m. — M Street Park, South Boston
- 3:00 p.m. — Beach Street and Harrison Ave, Chinatown
- 4:00 p.m. — Paul Revere Mall, North End
- 5:00 p.m. — Winthrop Square (the Training Field), Charlestown
- 6:15 p.m. — Maverick Square, East Boston
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