South Boston Christmas Stroll

Thursday, December 3 · 4:00–8:00 PM · Broadway, South Boston

Southie’s favorite night of the season is back. On Thursday, December 3, Santa leads the procession up Broadway in an antique fire truck, the tree lights up at the Library, carolers stroll the sidewalks, and Broadway’s shops and restaurants throw their doors open with holiday specials all evening.

Follow Santa up Old Colony and Dorchester Street onto East and West Broadway — there’s hot chocolate and treats waiting at every stop.

Santa’s Stops

  • 4:15 PM — Medal of Honor Park

  • 4:45 PM — Library on East Broadway (tree lighting!)

  • 5:15 PM — West Broadway Municipal Parking Lot

  • 5:30 PM — Corner of C Street and West Broadway

Stroll the Specials

These Broadway businesses are celebrating with Stroll-night specials — and more are joining every week:

  • Bohdii Boutique (398 W Broadway) — 15% off storewide + sip & shop

  • Clover Clubhouse (368 W Broadway) — $10 Open Play, 4–6 PM — warm up while you wait for Santa to reach West Broadway

  • Covet (391 W Broadway) — 20% off standard items, 10% off luxury items (in-store), complimentary prosecco & sparkling rosé

  • Habit (703 E Broadway) — drinks, snacks & a gift with purchase, 4 PM till the end of the Stroll

  • Harry and Lou (735 E Broadway) — 15% off storewide

  • Layla’s American Tavern (332 W Broadway) — donut holes & hot cocoa outside

  • Native Sun (538 E First St) — special in-store promotion & free raffle

  • Stapleton Floral (635 E Broadway) — free 12-inch wreath with a traditional bow ($35 value) with any purchase of $55 or more

Bundle up, bring the family — and Shop, Dine & Celebrate Southie.

Presented by the South Boston Chamber of Commerce & SBNDC