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!

Snowport Holiday Market
When: November 10th – December 31st
Where: 100 Seaport Boulevard
Highlights: 120 + vendors, holiday activities, and a tree market

South Boston Holiday Stroll
When: Thursday, November 30 from 4-6 p.m
Where: Local businesses and restaurants in South Boston
Highlights: Santa on an antique fire truck, followed by a Classic Cadillac convertible with up-and-coming pop singers Carly Underwood and Tyler Levs of MusicBall Entertainment. More than 50 participating businesses will be offering incredible savings on November 30th; look for the big red bow on their storefronts.

Christmas + Holiday Market at the Lot
Shop local this season and head to The LOT for the final event of 2023! Event will include local businesses, Santa photos, festive drinks + treats!  Learn more here!

South Boston Catholic Academy Jingle Bell Run
The 14th Annual Jingle Bell Run will be held on Saturday, December 2nd at 10 am. There will be two youth races at 9 am, 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. After the race, there will be refreshments, food, entertainment, and awards. Sign up and get more info here!

Laboure Christmas Shoppe
Shop Christmas decorations, holiday decor and more, all the benefit the Laboure Center in South Boston.  Take place Saturday and Sunday 10am-2pm at the Laboure Center located at 275 West Broadway.

Harpoon Holiday Market
When: December 9th from 12pm-5pm
Where: Harpoon Brewery
Highlights: Boston Women’s Market and lots of Harpoon Beer

2nd Annual Cisco Stroll
The Cisco Stroll will take place on Saturday, December 9th from 12-4pm. There will be exclusive scarf giveaways, a holiday costume contest, a window decorating contest, and Cisco brews. For every pint of Cisco sold, $1 will be donated to the South Boston Neighborhood House. Loco, Lincoln, Layla’s, Publico, Fresh, Roza Lyons, Hunters, and The Broadway are participating bars. Stop by your favorite bar for a Cisco and a good time.  You can get the details here! 

The Greg Hill Foundation Jingle All the Way 5k
The Jingle All The Way 5K is back and coming to Boston’s Seaport! So, dig out your ugly sweaters, winter hats, and running shoes and join us on Saturday, December 9th for a holly jolly 5K. Post-race we’ll be sure to have a festive post-race celebration with live music, delicious food, and amazing drinks. Wearing your favorite holiday outfit is also strongly encouraged as we will be rewarding some of the best-dressed runners

Grinch Brunch at City Tap
Bring your resting Grinch face to City Tap House because ‘tis the season to host a brunch honoring the reformed Christmas villain. On December 9, City Tap will be transforming into Whoville and Mount Crumpit for a holiday happening filled with green grumps and jolly Whos. Deck City Tap’s halls with holiday sweaters and reindeer jammies and while DJ J-Wall spins the best (or if you’re feeling extra-Grinchy, the most painful) holiday tunes, it’s time to get your sip and snack on. Paying ode to the Grinch’s faithful four-legged friend, chow on Max’s French Toast Sticks with green scrambled eggs ($6). Other options are Cindy Lou’s Green Eggs & Bacon, green scrambled eggs with bacon ($7), and green Grinch Waffles with syrup and whipped cream ($8). For liquid merriments, there’s an Eggnog Martini with Stoli Vanil and Galliano ($14); Hot Cider, fresh apple cider spiked with Sailor Jerry rum ($12; virgin available for $6); Hot Chocolate with whipped cream ($6) or double down and lace it with Sailor Jerry rum ($12); and Mule Log with Jameson Black Barrell, cranberry sauce and lime garnished with a mini Christmas tree AKA spring of rosemary ($13).  Make your reservation today! 

Kids Cookie Decorating Night at The Broadway
Join The Broadway for a fun night of cookie decorating on Monday, December 4th and December 11th, from 5 to 7pm. The ticket is $10 and includes cookies, decorating supplies, and a to-go box to take your creations home. It is the perfect way for the kids to enjoy the holiday season. Get your tickets here!

Holiday Paint N Sip at Shy Bird
DIY Custom Sneaker Paint Night at Shy Bird on Monday, December 4th at 6pm – you can purchase your ticket here! Grab a pair of sneakers and head to shy bird south boston to customize your kicks. Jenna from J Lenore designs will guide you through the process of customizing your sneakers, providing tips and tricks along the way! 🎄 Featuring a special holiday drink menu available for purchase, along with your favorite shy bird snacks (yes, dunks). It is highly recommended that you use a mostly white, leather/faux leather-based sneaker, but canvas is also a great option. More details on Eventbrite – ticket price does not include food, beverage, or Eventbrite fee.

Capo x Market Floral Studio-Holiday Wreath Workshop
Market Floral Studio will be taking over Capo for a Holiday Wreath Workshop on Monday, December 4th at 7pm. You will be creating a beautiful holiday wreath with fresh juniper berries, incense cedar, eucalyptus, pinecones and other fun accessories. It is a great experience for a date night or a group activity. Get your tickets here!

The Broadway Holiday Showcase
The Broadway Holiday Showcase will be held on Wednesday, December 6th from 6-9 pm. The night will be filled with local vendors, food, and drink. The vendors included are CAN’DL, Self Centerx, The Point, Project Paulie, The Attic, Agape, 4103 Designs, Vester, Love Child, Maker Scholar, Bodhi Boutique, Deir Fiur Home, In Good Co., Niraji, Camden Hydes, Wolfie’s All Natural Treats, and MW Hair Studio. There will be a special collaboration with OLIPOP and there will be a complementary OLIPOP cocktail.

Linda Huey Holiday Pottery Sale and Party
Linda Huey Pottery Studio – 249 A Street Cooperative artist building – Saturday and Sunday, December 9th and 10th, Noon to 5:00 pm each day – Find a meaningful handmade gift and enjoy holiday cheer in a party atmosphere at Linda Huey’s pottery sale. There will be a large assortment of pottery and sculpture, from small, affordable gifts to 7-foot-tall sculptures. There will be homemade cookies, punch, and goody bags to take home. In addition, the 249 A Street Gallery on the ground floor will have a “Paperclips” show with more than fifty small works under $200 by 249 A Street artists. For more info, go to

Wreath Making at The Broadway
Love Child will be hosting a wreath-making workshop at The Broadway on Tuesday, December 12th at 7pm. The ticket will include the materials to make the wreath. The Broadway will also be serving festive food and drinks at an additional cost. Get your tickets here!

Love Child Holiday Wine Tasting
On December 15th at 6pm enjoy a festive vino tasting with snacks and all the holiday vibes!  You can get your tickets here!

Fresh Boston Holiday Events
Fresh Boston is definitely in the Holiday spirit. They will be offering a plethora of Holiday events in the month of December. From a Sip and Shop to Brunch with Santa, they have it all! Check them out below!


Did we miss your festive event? Let us know! [email protected]



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