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Mayor Wu Announces 2023 Enchanted Trolley Tour

Enchanted Trolley Tour continues festive tradition of lighting holiday trees and spreading joy throughout neighborhoods


Mayor Michelle Wu today announced the schedule for this year's Enchanted Trolley Tour, a Boston holiday tradition of lighting trees throughout the city to spread joy. This year, the Mayor’s Enchanted Trolley Tour will take place on Saturday, December 2 and Sunday, December 3, in neighborhoods throughout Boston. This event is presented by Bank of America with a special thanks to CityView Trolley Tours and includes visits with Santa, Mayor Wu, Office of Neighborhood Services staff, tree lightings, and more.

"This time of the year is the perfect time for community to come together and celebrate, and I encourage Boston residents across our neighborhoods to join us as we kick off the holiday season with our annual Enchanted Trolley Tour,” said Mayor Michelle Wu. “I’m grateful to our partners for their valuable support for Boston to continue this treasured tradition and opportunity to connect with constituents."

The 2023 Mayor’s Enchanted Trolley Tour schedule is as follows: 

Saturday, December 2, 2023

  • 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 3, 2023

  • 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


“The Enchanted Trolley Tour is more than just an event; it expresses the joy of the holiday season and brings people together from every neighborhood of the city in a spirit of good cheer. Bank of America is proud to join Mayor Wu and the City of Boston in celebrating the magic of the holidays by supporting the 2023 Enchanted Trolley Tour and Tree Lightings,” said Miceal Chamberlain, President, Bank of America Massachusetts.

The Mayor’s Enchanted Trolley Tour is now in its 27th year. Residents are encouraged to join in the free tradition to unite with community members of all ages and to embrace the holiday season. 

“The Enchanted Trolley Tour brings families countless memories and happiness,” said Miguel Vargas, Executive Director of East Boston Main Streets. “See you on December 3 for our stop on the annual trolley tour with Mayor Michelle Wu.”

Follow the Mayor’s Office of Tourism, Sports, and Entertainment on social media @VisitBostonCity and visit to learn about more free, family-friendly events happening in the City of Boston.

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