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Enchanted Trolley Tour 2023


Enchanted Trolley Tour


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Dec 2 - 3

Times Vary



Throughout Boston

Get in the holiday spirit with Boston's Enchanted Trolley Tour! For two days, families can hang out with Santa, watch dazzling tree lightings, and get swept up in the magic of the season. The tour has a total of 16 stops over the weekend. It starts in West Roxbury, and ends in East Boston.

Find your neighborhood below...

Day 1 | Saturday, December 2, 2023

  • 11:00am - Hastings Lot, West Roxbury 

  • 12:00pm - Wolcott Square, Readville

  • 1:00pm - Mattapan Square

  • 2:00pm - Hyde Square, Jamaica Plain 

  • 3:00pm - J.P. Monument, Jamaica Plain

  • 3:45pm - Brigham Circle, Mission Hill

  • 4:30pm - Bolling Building, Roxbury

  • 5:45pm - Blackstone Square, South End

  • 6:45pm - Oak Square, Brighton

Day 2 | Sunday, December 3, 2023

  • 12:00pm - Codman Square, Dorchester

  • 1:00pm - Adams Corner, Dorchester

  • 2:00pm - M Street Park, South Boston

  • 3:00pm - Beach Street and Harrison Ave, Chinatown

  • 4:00pm - Paul Revere Mall, North End

  • 5:00pm - Winthrop Square (the Training Field), Charlestown

  • 6:15pm - Maverick Square, East Boston

Books You May Love...

The following stories are geared towards younger readers and families who love picture books.

Brown Sugar Baby Christmas Joy
Christmas Is Every Day (An Every Day Together Book)
If It's Christmas and You Know It
The Biggest Little Boy a Christmas Story

Boston Month-By-Month

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About FamilyFun

We're collecting cool experiences in (and around) the city -- and sharing them with you! Think of us as matchmakers between awesome programming and young families looking to create sweet memories! 

If you're ever looking for kid-friendly events — we’ll be here!! You can visit our calendar anytime to find tons of free (and close to free) things to do in Boston.

While we try our best to update content, information changes faster than we can keep up.
For example, events have been cancelled or postponed due to low-to-no attendance, weather, and other emergencies. We may also unintentionally make a mistake. Please confirm details before heading out with your little one(s). You can do so by clicking on the "source" button below the map above. If you choose to sign up for different events, the organizations will often reach out to you directly.

Event images belong to their respective owners and are used under CC BY-SA 3.0. If you know of an event you think our visitors will love, please let us know here.  And if we listed your event and you would like it removed, please reach out here.

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