Festive Events in the Neighborhood

It’s so important to support our small business community! Here are some festive events and pop-ups happening in the neighborhood! Check back, as this list will be updated!

Get your tickets to the Caught in Southie Festive Stoop Stroll

Caught in Southie is hosting the second Annual Caught in Southie Holiday Stoop Decorating Competition + Festive Stroll, and you’re invited to join the merriment on Saturday, December 13th at 4 pm! This one-of-a-kind event is your chance to explore the neighborhood, admire some seriously impressive holiday decor, and enjoy the warm hospitality of participating homes. Each stop will offer festive refreshments and entertainment to keep the holiday vibes strong. And all proceeds benefit the South Boston Neighborhood House! Plus, there will be a trolley to hop on and off! Get your tickets here! 

The Annual Christmas Stroll in South Boston

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.  Get all the details here including Santa!

Light Up Seaport

Friday, December 5th

Light Up Seaport is the perfect way to kick off the Holiday Season. The event will be held on Friday, December 5th, from 5-9pm. Now in its seventh year, the community event will feature a tree lighting, live entertainment, and can’t-miss offers and surprises from Seaport’s incredible mix of retailers and restaurants. You can get the full details here! 

Enchanted Trolley Tour and Tree Lighting

Sunday, December 7th

Mayor’s Tree Lighting at Medal of Honor Park will take place on Sunday, December 7th at 2pm.  Enjoy hot cocoa, face painting and more!

Massport Winter Festival

Celebrate the season, support local, and experience the magic! Join Massport for a joy-filled celebration at the new 10 World Trade (401 Congress Street) in the South Boston Waterfront on Saturday, December 6th from 12pm-5pm. All throughout the day, enjoy festive activities for all ages. Perfect for families, friends, and neighbors.

Hunter’s Holiday Tree Lighting

Join Hunter’s for their 3rd Annual Tree Lighting on Wednesday, December 3rd at 8pm. Enjoy awesome music by It’s Ya Boy KR. There will be festive drinks and specials. The cozy cabin will be decked out for the holiday season! Make your reservation here!

Lincoln x Market Floral Studio Holiday Wreath Workshop

Grab your friends and head over to Lincoln to create a Holiday masterpiece. Market Floral will be leading a Wreath Workshop on Monday, December 1st at 7pm. The class is $75 and includes step by step instruction to create a beautiful holiday wreath with fresh juniper berries, incense cedar, eucalyptus, pinecones and other fun accessories. Secure your tickets now!

Merry Moakley

Boston Harbor Now is excited to co-host Merry Moakley for its third year, thanks to the support of the City of Boston Parks and Recreation Department, South Boston en Acción, South Boston Neighborhood House, the Boston Family Engagement Network, and Volo.  A family-friendly evening of festive outdoor fun featuring food, crafts, live music, free books, photos, games, and more! Thursday, December 12th, from 3:30 pm – 5:30 pm South Boston Neighborhood House Preschool Parking Lot, 1187 Columbia Road, Boston, MA For more information about Merry Moakley, Moakley Park, and a complete schedule of winter activities happening on the Boston Harbor waterfront, visit here. 

Breakfast with Santa at Publico

Santa is coming to town!! Santa will be at Publico on December 6th, 13th, and 20th for a family-friendly breakfast! There will be a full breakfast buffet and festive holiday cocktails for the adults. Secure your spot now! 

The Winter Market at Publico

Step inside a winter wonderland at Publico! They have created an enchanting 360° installation inside Publico’s Garden! This wonderland installation features lush winter greenery, a jaw-dropping 16-foot dazzling lit Christmas tree, twinkling holiday lights, and festive and fun ‘holiday market’ inspired drinks and snacks! It is the perfect way to get into the holiday spirit. Make your reservation here!

South Boston Catholic Academy Jingle Bell Run

The 15th Annual Jingle Bell Run will be held Saturday, December 13th at 10 am. There will be 2 youth races at 9am, featuring a 100 meter dash for kids 9 and under and a ½ mile race for kids 14 and under. The main event is a 5km run along the beaches and around castle island. There will be refreshments, food, entertainment, and awards after the race. Sign up and get more info here!

Holiday Wreath Workshop at Loco

Stop by for a Sunday fun-day at Loco on Monday, December 8th at 6:30pm ! Jump into the holiday spirit and come create your own winter greenery wreath- no previous experience required! Owner and lead designer Kayla Ciavarra of BUDS Floral Design will guide you in a step-by-step instructed class to create a hand tied greenery wreath to bring home for the holidays. Decor items such as ornaments, bows + other decorative items will also be provided to make your wreath truly unique. Loco’s full brunch menu will be available to enjoy during class! Get your tickets here!

Capo Sip & Shop

Get ready to sip, shop, and be merry at Capo! Their Sip & Shop will be held on Saturday, December 6th from 11am to 3pm. There will be 20+ local vendors, delicious food and drink, and holiday cheer!! It is free so stop by for a festive event.

Buttercream Boston Holiday Pop-up

Buttercream Boston will be popping up at Dirty Italian with holiday deliciousness! They will be serving holiday cake slices. Flavors will include “Minty Mallow”, “Chai-nog”, “Snowball”, and more! The pop up will be on Saturday, December 6th from 10am to 12pm. Get all the details here!

Loco’s Holiday Sip & Shop 

Loco will be hosting a Sip & Shop in the 410 lounge on Sunday, December 14th from 3 to 6pm. There will be over 12 local stores participating. It is a great way to get some last minute gift shopping done and enjoy a margarita or two! 

Holiday Market at Castle Island Brewery

Celebrate local creativity all season long at our Shop Local Market at Castle Island Brewery in South Boston, happening every Saturday from 12–5 for four consecutive weeks. Each weekend, you’ll discover a fresh mix of local vendors offering unique gifts, handcrafted goods, and one-of-a-kind finds that are perfect for everyone on your list—or for treating yourself. Enjoy a cold beer, grab a bite to eat, and soak in the festive atmosphere as you explore the best of what local makers have to offer. It’s the perfect way to spend your Saturday supporting small businesses and spreading some holiday cheer.

Holiday Movie Night at Capo

Christmas classics will be playing every Monday in December at Capo! There will be two showings, one for the kids at 5:30pm and one for the adults at 7:30pm. There will be hot chocolate with the option of having it spiked for adults!! Get cozy at Capo and get in the holiday spirit. Check out the line up on their instagram!

Clover Clubhouse Holiday Sip & Shop

Clover Clubhouse will be hosting a Sip & Shop on Tuesday, December 9th from 6 to 9pm. There will be local vendors, light bites, and a cash bar! It is the perfect place to check some Christmas shopping off and have a fun night! 

4th Annual Cisco Stroll

The Cisco Stroll will take place on Saturday December 13th from 12-4pm. There will be exclusive scarf giveaways, live music, holiday decor contest, and cisco brews. For every pint of Cisco sold, $1 will be donated to the South Boston Neighborhood House. The participating bars are Roza Lyons, The Playwright, and The Broadway. Stop by your favorite bar for a Cisco and a good time. Get all the details here!