Holiday Train Show at Grand Central Terminal
Grand Central Gallery Annex - 10:00 AM
Grand Central Gallery Annex - 10:00 AM
Sloomoo Institute
Sloomoo Institute - 10:00 AM
Sloomoo Institute - 10:00 AM
Calypso, Carols, and Cocoa: The Dumbo Holiday Lighting
The Archway Under The Manhattan Bidge - 4:00 PM Pick
The Archway Under The Manhattan Bidge - 4:00 PM Pick
North Pole Express in Manhattan
TopView Sightseeing
Tea Around Town + NYBG Holiday Train Show
Central Park South bus stop
Bay Ridge Prep Upper School Open House
Bay Ridge Prep Upper School
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Mayor's Enchanted Trolley Tour
Sat Dec 6, 2025 - Sun Dec 7, 2025
- see all dates
Repeating every days through December 7, 2025.
Various times
Age: All ages
Price: Free
For the 29th year, the Mayor's Enchanted Trolley Tour will continue the festive tradition of lighting holiday trees while bringing holiday spirit to children across Boston. The event includes visits with Santa, tree lightings, and more.
SATURDAY, DECEMBER 7
- 11 a.m. - Hastings Lot, West Roxbury
- 12 p.m. - Wolcott Square, Readville
- 1 p.m. - Mattapan Square
- 2 p.m. - Hyde Square, Jamaica Plain
- 3 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
- 12 p.m. - Codman Square, Dorchester
- 1 p.m. - Adams Corner, Dorchester
- 2 p.m. - M Street Park, South Boston
- 3 p.m. - Beach Street and Harrison Ave, Chinatown
- 4 p.m. - Paul Revere Mall, North End
- 5 p.m. - Winthrop Square (the Training Field), Charlestown
- 6:15 p.m. - Maverick Square, East Boston
This year, the Mayor's Enchanted Trolley Tour will run from Saturday, December 6, to Sunday, December 7, in neighborhoods throughout Boston. ( *Please note that no one rides the trolley apart from working staff and the Christmas characters. )
** Activity dates/times are subject to change. Please click through to the activity website to verify.
