Boston's longest-running holiday tradition on wheels is marking a milestone this winter. Mayor Michelle Wu and the Mayor's Office of Tourism, Sports and Entertainment have announced the 30th Annual Enchanted Trolley Tour, which is expected to roll through 16 neighborhoods across the city on Saturday, December 5, and Sunday, December 6.
The anniversary tour continues three decades of pairing neighborhood tree lightings with Santa visits, according to EIN News. Wu said the tour has brought holiday magic to Boston neighborhoods for 30 years, and she thanked neighborhood partners and Bank of America for helping keep the tradition going. Each stop is expected to feature giveaways along with visits from Santa, Wu herself, and staff from the Office of Neighborhood Services.
Who's Behind the Ride
Bank of America presents the Enchanted Trolley Tour, with Cityview Trolley Tours supporting the event. Miceal Chamberlain, president of Bank of America Massachusetts, called the tour a holiday highlight that delights residents and visitors of all ages, and said Bank of America looks forward to the event every year and is proud to join Wu and the city in welcoming back the tour and its tree lightings.
The route is dense with stops packed into two afternoons and evenings. On Saturday, December 5, the trolley is slated to hit Hastings Lot in West Roxbury at 11 a.m., Wolcott Square in Readville at noon, Mattapan Square at 1 p.m., Hyde Square in Jamaica Plain at 2 p.m., J.P. Monument in Jamaica Plain at 3 p.m., Brigham Circle in Mission Hill at 3:45 p.m., the Bolling Building in Roxbury at 4:30 p.m., Blackstone Square in the South End at 5:45 p.m., and Oak Square in Brighton at 6:45 p.m.
Sunday's Route Across the City
Sunday, December 6 continues the circuit with a fresh set of neighborhoods. Stops are expected at Codman Square in Dorchester at noon, Adams Corner in Dorchester at 1 p.m., M Street Park in South Boston at 2 p.m., Beach Street and Harrison Avenue in Chinatown at 3 p.m., Paul Revere Mall in the North End at 4 p.m., Winthrop Square (the Training Field) in Charlestown at 5 p.m., and Maverick Square in East Boston at 6:15 p.m.
Earlier tours have followed a similar pattern. A Boston city government announcement for the 28th Annual Enchanted Trolley Tour, held in December 2024, listed a schedule that included Hastings Lot in West Roxbury, Mattapan Square, and the J.P. Monument in Jamaica Plain among its stops, showing the route has long touched many of the same corners of the city.
Tree Lightings and a Car-Free Newbury Street
Separately, the city is set to host holiday tree lightings in parks in the North End, Back Bay, and South Boston between November 23 and December 3. Newbury Street is expected to go car-free on December 6 from 10 a.m. to 6 p.m., with the city encouraging businesses along the corridor to offer outdoor family-friendly activities, pop-up parklets, and brand activations. If inclement weather forces a postponement, that Newbury Street programming would be rescheduled to December 13.
City traffic advisories from past years give a sense of what logistics typically look like around the tour. A City of Boston traffic notice published in 2025, posted at content.boston.gov, described the December 7–8, 2024 trolley tour as starting and ending at Boston City Hall and detailed parking restrictions in West Roxbury along Centre Street.
The Mayor's Office of Tourism, Sports and Entertainment, which organizes the tour alongside Bank of America and Cityview Trolley Tours, says its broader mission is to strengthen Boston's tourism industry by producing events, supporting film and TV production, and marketing the city to conventions and visitors, while also promoting participation in public celebrations like this one.
