10 Enchanting Holiday Strolls Coming to Boston in December 2023 [12/01/23]

Embark on a festive journey through Boston's neighborhoods with our curated list of the 10 most enchanting holiday strolls in December 2023. Explore festive local shops, immerse yourself in holiday tunes, savor seasonal drinks and bites, and much more.

Events listed chronologically

1) Jamaica Plain Holiday Stroll

When: Thursday, 11/30 at 5pm

What: Join the 2nd annual JP Holiday Stroll with Santa and live tunes from the JP Honk Band. Shop at participating stores for exclusive discounts, treats, and a chance to win a $1,000+ gift basket (Taylor Swift album included).

2) North End Holiday Stroll

When: Friday, 12/1 at 5pm

What: Celebrate the magic of the season at the 16th annual North End Holiday Stroll featuring a tree lighting, food, drinks, and many more festive activities.

3) Holiday Stroll at Boston Landing

When: Saturday, 12/2 at 11am

What: Experience the magic with Mr. & Mrs. Claus, carolers, hot cocoa, and a multicultural celebration. Shop local, enjoy live tunes, and partake in all the family fun.

4) South End Holiday Stroll

When: Saturday, 12/2 at 11am

What: Shop, dine, and discover festive finds with 100+ local businesses. Don't miss the holiday tree lighting at Blackstone Sq at 5:30pm, where the Mayor’s Enchanted Trolley Tour will join the celebration, along with Mr. & Mrs. Santa Claus, other holiday characters, and holiday music.

5) Union Square Holiday Stroll

When: Saturday, 12/2 at 12pm

What: Discover unique gifts, support local businesses, enjoy tasty treats and decorative storefronts, and conquer the Stroll the Square Challenge for a chance to win cash prizes.

6) Prudential Center Holiday Stroll

When: Saturday, 12/2 at 4pm

What: Stroll through the Pru and discover exclusive discounts, enjoy holiday-themed sip stations, and groove to festive tunes by electric violinist Vivian Luo. Stop by and take a photo with Santa in his favorite Back Bay living room.

7) Holiday Stroll at Boston Design Center

When: Thursday, 12/7 at 4pm

What: Indulge in cocktails, culinary delights, and musical vibes as you explore the Boston Design Center's array of designers and showrooms.

8) Beacon Hill Holiday Stroll

When: Thursday, 12/7 at 5pm

What: Embrace the holiday magic at Beacon Hill Holiday Stroll as Charles Street is close to traffic and open for festive fun. Shop local shops, take photos with Santa (from 3-5:30pm), enjoy refreshments, sing along to live music, and watch the holiday tree lighting celebration.

9) Ice Sculpture Stroll at Assembly Row

When: Thursday, 12/7 at 6pm

What: Explore nine whimsical ice sculptures scattered around the Row. Grab a festive map, snag holiday goodies at each sculpture, and exchange your completed map for a FREE Christmas ornament.

10) Speedway Holiday Stroll

When: Saturday, 12/9 to Sunday, 12/10 at 12pm

What: The Charles River Speedway is hosting Speedway Holiday Stroll the entire second weekend of December 2023. The festivities include two holiday markets, gingerbread house building, ornament decorating and winter crafts, a Negroni lounge, mulled wine, craft brews from Notch, delicious bites from on-site vendors, and so much more.

See our other curated holiday roundups:

10 Enchanting Holiday Strolls Coming to Boston in December 2023

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