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By Scott Roberto / November 14, 12:00 AM
High 5: Holiday Strolls


Join a festive jaunt to enjoy a sparkling view of the Hub this joyous season


Historic Holiday Stroll (pictured): On Fridays and Saturdays at 3:30 p.m. from November 18–December 30, this Freedom Trail-hosted walk, led by guides in Victorian Era costumes, explores Boston’s 19th century history along the famed, brick-marked pathway. Marvel at holiday lights, illuminated trees and more while visiting such sites as the Old South Meeting House, Old State House, Old North Church and the Paul Revere House.


North End Holiday Stroll: Partake in the 16th annual tradition December 1 from 5–9 p.m. in Boston’s bastion of Italian culture. Eat, drink and be merry at 15 mom-and-pop restaurants, shops, galleries and cafes while enjoying the seasonal scenery, as well as a tree lighting at the corner of Hanover and Cross streets.


Boston Landing Holiday Stroll: Hop over to the Brighton area December 2 from 11 a.m.–3 p.m. for a family-friendly day featuring pictures with Mr. and Mrs. Claus, caroling, hot cocoa and shopping galore from local retailers as well as special pop-up vendors. If it snows, don’t fret—it only adds to the fun as possible snowball fights and snowman-building contests could be in the works.


South End Holiday Stroll: Also on December 2, this event traverses the area, with pop-ups offering cider, cocoa and gift wrapping help at spots on Tremont and Washington streets; tours, organ music, a petting zoo and an appearance by St. Nick at the Cathedral of the Holy Cross; a tree and wreath sale at Blackstone and Franklin squares; a trolley tour and tree lightings with Mayor Michelle Wu; and more shopping and dining opportunities than the number of Santa’s reindeer and nights of Hanukkah combined.


Holiday Sights & Festive Nights Trolley Tour: Give your feet a bit of a break by hopping on a heated vehicle from Old Town Trolley December 1–30 to experience sights, sounds and storytelling courtesy of costumed guides who escort visitors to magical destinations in and around Boston Common and Beacon Hill. 

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