The South Boston Chamber of Commerce and South Boston Neighborhood Development Corporation are excited to once again make the Broadway business district and surrounding areas a festive place for the community to shop and dine locally during the holiday season.

The annual South Boston Christmas Stroll will take place on Thursday, Dec. 4, starting at 4 p.m., officially kicking off the “Shop, Dine, and Celebrate” campaign, a month of holiday activities that encourage everyone to support local businesses and restaurants throughout the season.

“The Christmas Stroll is one of South Boston’s most beloved traditions, bringing neighbors together while highlighting the incredible small businesses that make our community so special,” said Jenni McNeill of the South Boston Chamber of Commerce and South Boston NDC. “We’re thrilled to kick off a full month of holiday activities that celebrate the season and the spirit of shopping local.”

This year’s Stroll will feature Santa Claus riding through South Boston on an antique fire truck, followed by an up-and-coming MusicBall singer spreading holiday cheer. Santa’s route will take him up Old Colony Avenue to Dorchester Street, with four stops along wreath-adorned East and West Broadway where families can enjoy hot chocolate, treats, and photo opportunities:

 4:15 p.m. — Medal of Honor Park
 4:45 p.m. — South Boston Branch Library (where Santa will light the tree!)
 5:15 p.m. — West Broadway Municipal Parking Lot
 5:45 p.m. — Corner of C Street and West Broadway

Adding to the holiday magic, The Original Dickens Carolers will stroll and sing along Broadway from
4–6 p.m.

Check the Chamber’s Instagram (@SouthBosChamber) for participating businesses that will offer special savings and promotions on Stroll night. The month-long celebration includes the 12 days of giveaways featuring gifts from our amazing Chamber members! This is just another way to celebrate our community, highlight our local businesses, and spread a little extra joy in South Boston this holiday season.

Each day from Dec. 10–21, the Chamber will post a new holiday giveaway — and entering is super
easy:

 Follow @SouthBosChamber on Instagram
 Like the daily giveaway post
 Tag a friend in the comments (each tag = an entry!)
 Bonus: Share the post to your story for extra holiday cheer

Participants can win local gifts, treats, gift cards, services, and festive surprises from South Boston
small businesses!

Stay tuned each morning — you won’t want to miss the giveaways!

There will also be a festive photo session for dogs, perfect for holiday cards and family fun, on Saturday, Dec. 6 at 739 E. Broadway from noon to 3 p.m.

Join us as we celebrate the season, support our neighborhood businesses, and spread holiday joy throughout South Boston!

We are grateful to the sponsors who helped decorate Broadway with festive wreaths:
 Massachusetts Port Authority
 Stapleton Floral
 The Cedarwood Group
 The City of Boston