14 Enchanting Holiday Strolls Coming to Boston in December 2024 [11/26/24]

Embark on a festive journey through Boston's neighborhoods with our list of the 14 most enchanting holiday strolls in December 2024. Explore festive local shops, immerse yourself in holiday tunes, savor seasonal drinks and bites, and much more.

Events listed chronologically

1) Open Newbury Street Winter 2024: Holiday Edition

When: Sundays 12/1 and 12/8

What: For two Sundays this December, Newbury Street will be closed to cars for a festive, pedestrian-only shopping experience complete with hot chocolate stands and live entertainment.

2) Holiday Stroll at Boston Design Center

When: Tuesday, 12/3

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

3) Time Out Market Holiday Stroll

When: Wednesday, 12/4

What: Following the Fenway neighborhood tree lighting, head to Time Out Market to meet Santa, listen to festive music, and enjoy holiday themed food and beverage specials from the market vendors.

4) South End Holiday Stroll

When: Wednesday, 12/4

What: Shop, dine, and discover festive finds with 100+ local businesses. South End shops will stay open late and offer an extra dose of holiday cheer during this beloved annual event.

5) South Street Holiday Nite Market

When: Thursday, 12/5

What: The South Street Holiday Nite Market (the chic new edition of the JP Holiday Stroll) features live entertainment and seasonal food and beverages while you stroll South Street shopping and perusing artisan goods.

6) South Boston Holiday Stroll

When: Thursday, 12/5

What: Patronize local South Boston businesses and restaurants during this festive evening. But first, catch Santa’s arrival in an antique firetruck and watch as he makes his way through the neighborhood, lighting the local tree along the way.

7) Beacon Hill Holiday Stroll

When: Thursday, 12/5

What: Charles Street will be closed to traffic between Cambridge Street and Beacon Street for maximum festive cheer during this holiday stroll. Shop local shops, introduce your young ones to Santa (who will be at Hill House 3 to 5pm), sip piping hot chocolate, and listen to live music from the Brass Quartet.

8) Ice Sculpture Stroll at Assembly Row

When: Thursday, 12/5

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.

9) Union Square Holiday Stroll

When: Saturday, 12/7

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.

10) Speedway Holiday Stroll

When: Sunday, 12/8

What: More than 30 woman-owned businesses will pop up at The Speedway for this festive stroll event. While you shop, enjoy seasonal bites like a cinnamon sugar pretzel from Notch Provisions and hot and cold sake from Koji Club. Plus check out ornament decorating, holiday movie screenings, and a gingerbread house competition.

11) North End Holiday Stroll

When: Friday, 12/13

What: Celebrate the magic of the season at the 17th annual North End Holiday Stroll featuring a tree lighting, food, drinks, and many more festive activities.

12) Charlestown Holiday Night Out

When: Wednesday, 12/11

What: Walk down Main Street in Charlestown getting a jump on your holiday shopping. Businesses will be open late and offering special discounts as well as holiday specials for the occasion.

OUTSIDE OF BOSTON

13) Dedham Square Holiday Stroll and Gift Market

When: Friday, 12/6

Where: Dedham | 22.7 miles from Downtown Boston

What: Meet Santa, Mrs. Clause and Elfie at this beloved annual holiday stroll. Listen to holiday music from musicians and live carolers, pop into local shops, and enjoy all the seasonal decor.

14) Wayland Town Center Holiday Stroll & Tree/Menorah Lighting

When: Saturday, 12/14

Where: Wayland | 19.2 miles from Downtown Boston

What: Gather with friends and neighbors on the Wayland Green to see the holiday tree and Menorah lit for the season. Santa will attend with friends and you can have a cup of hot cocoa with local law enforcement while you wait.

See our other curated holiday roundups:

14 Enchanting Holiday Strolls Coming to Boston in December 2024

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