Boston

Mayor Michelle Wu Announces 29th Annual Enchanted Trolley Tour Across 16 Neighborhoods

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Published on November 20, 2025
Mayor Michelle Wu Announces 29th Annual Enchanted Trolley Tour Across 16 NeighborhoodsSource: Facebook/Mayor's Office of Tourism, Sports, and Entertainment for the City of Boston

Mayor Michelle Wu has confirmed the schedule for Boston's 29th Annual Enchanted Trolley Tour, set to usher in the holiday season with community spirit and festive fun. The two-day event will feature the traditional tree lighting ceremonies and Santa visits, a mainstay for 16 local neighborhoods. According to a release from the city's official website, the tour aims to knit communities together with a splash of holiday cheer on December 6 and 7.

The time-honored Trolley Tour will cover various Boston neighborhoods, from West Roxbury's Hastings Lot to East Boston's Maverick Square, celebrating with locals and Mayor Wu, who, in a statement made by the City of Boston's official website, expressed excitement about the upcoming festivities. "The annual Enchanted Trolley Tour is a beloved annual tradition bringing families together across the city to kick off the holiday season," Mayor Wu said, adding anticipation for the weekend's celebrations and gratitude towards participating partners.

Bank of America marks its return as this year's presenting sponsor, collaborating with CityView Trolley Tours to deliver an enchanting experience. Miceal Chamberlain, President of Bank of America Massachusetts, emphasized the significance of the event, which is unique to Boston's community culture, bringing an endearing charm and holiday delight to the region, as he told the City of Boston's official website.

The tour will commence on December 6 at 11:00 a.m. in the Hastings Lot and will continue its journey, making stops at locations like Hyde Square, Mattapan Square, and culminating for the day at Oak Square in Brighton, before resuming on December 7 starting at Codman Square in Dorchester and wrapping up at Maverick Square. The full schedule details can be found on the City of Boston's official website. The event promises a spread of giveaways and visits from Santa, alongside Mayor Wu and staff from the Office of Neighborhood Services, fostering a spirited sense of unity and celebration among Bostonians.

For those interested in more details and updates on the event, information can be accessed through the official channels of the Mayor's Office of Tourism, Sports, and Entertainment, which continues to support and promote tourism and local celebrations in Boston. Residents and visitors alike are invited to follow along on social media via the handle @VisitBostonCity or visit their website for the latest news and happenings around the city's tourism and entertainment scenes.