10 Enchanting Holiday Strolls Coming to Boston in December 2023
When:
Friday, Dec 01, 2023 5:00p -
Sunday, Dec 10, 2023 10:00p
Friday, Dec 01, 2023 5:00p -
Sunday, Dec 10, 2023 10:00p
Where:
Boston
Surrounding areas
Boston, MA
Admission:
FREE
Categories:
Date Idea, Festivals & Fairs, Kid Friendly, Outside, Photoworthy, Seasonal
Event website:
https://joyraft.com/search?q=holiday+stroll
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).
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.
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.
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.
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.
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See our other curated holiday roundups:
- The 30 Best Holiday and Christmas Markets in Boston 2023
- The 9 Best Outdoor Ice Skating Rinks in Boston: Winter 2023
- 10 Holiday Lighting Celebrations Coming to Boston in 2023
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