4.4 min readBy Published On: December 2nd, 2021Categories: See and Do0 Comments on Weekend Picks – December 3rd

South Boston Christmas Stroll

The South Boston Chamber of Commerce and the 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 Shop, Dine, and Splurge events run Thursdays, Dec. 2, 9, and 16. The festivities kick off on Thursday, Dec. 2, with the South Boston Christmas Stroll from 4:00-6:00 p.m., followed by shopping and dining at your favorite establishments. Santa will arrive on an antique fire truck, followed by a 1964 convertible and a singer provided by MusicBall Entertainment. You can learn more here! 

Light Up Seaport

Light Up Seaport & Holiday Stroll takes place on Friday, December 3, 2021, 5-9pm at Seaport Common, 85 Northern Ave.  Ready, set, glow! On Friday, December 3rd Boston Seaport’s 54-foot Norway Spruce tree adorned with 10,000 white lights will be lit. The tree lighting will be followed by a holiday stroll throughout the neighborhood. 40+ Seaport retailers will be offering one-night-only promotions. The tree lighting program will include performances by the Boston Children’s Chorus and other local entertainers. RSVP for the event via bostonseaport.xyz/snowport

Shore Leave Sippin’ Santa’s Surf Shack

Chosen alongside  22 other restaurants in the country to host the holiday event, the South End spot is converting for the Holiday season with their new list of holiday cocktails and brand new sushi menu designed to keep everyone satisfied and smiling! Make your reservation today to secure your very own lobster salad roll and Kris Kringle Colada!

Friday Holiday Brunch at The Broadway

Every Friday through the end of the year, The Broadway will be celebrating the holiday with a specialty brunch!  Enjoy holiday inspired items like Griddled Gingersnap Banana Bread, Egg Nog French Toast Sticks, Candy Cane Pancakes and specialty cocktails like the Clausmo – made with vanilla vodka, Kahlau mint mocha, Irish Creme, Creme de Menthe and cold brew. Available Fridays 11am-3pm.

Mayor’s Tree Light at Medal of Honor Park

Mayor’s Tree Lighting at Medal of Honor Park will take place on Sunday, December 5th from 12pm-2pm.  There will be pizza + snacks, Kick Off for Kids Candy Bar, Deja Brew Hot Chocolate, Bouncey house and obstacle course, Paw Patrol’s Chase + Marshall, Frozen’s Elsa + Olaf, Toy Story’s Woody and Buzz, balloon artist, DJ Kait, hover board raffle and more!

Cannonball Cafe is officially open

Located at 383 Dorchester Avenue, Cannonball Cafe – a new breakfast and lunch gathering spot designed and operated by chef Rachel Lazar is now open for business. Cannonball Cafe, whose name brings the revolutionary history back to South Boston and draws upon the forging and metallurgy that took place in the area, will brighten the longtime industrial district as its first dining spot! The new cafe is equipped with freshly brewed coffees, pastries, smoothies, and grab-and-go lunches. Cannonball Cafe offers discounts for veterans in addition to loyalty cards. Ask for one at checkout – 11th coffee is free!

Shop our Small Business Holiday Gift Guide

The neighborhood is full of amazing small businesses, makers and entrepreneurs offering unique goods and services. Caught in Southie wants to make it simple to shop local this holiday season. Our guide is filled with gift ideas including everything from home goods and jewelry to beauty products and gift cards! You can check it out here! 

Take a Stretch Class at MyStryde

On Sunday at 9:15am – enjoy a much needed 45 minute stretch class at MyStryde in Southie. $25 drop-in or $15 for members. You can register here! 

Deck the Halls – Decorate for the Holidays

Christmas is coming, it’s time to deck the halls!  Here are some places to pick up a tree, wreaths, ornaments and more! 

Making Spirits Bright

Peppermint, hot chocolate, egg nog, and vanilla! We don’t know about you, but these delicious flavors get us in the holiday spirit!  And here are some holiday inspired drinks we’re excited to try in the neighborhood! Check them out here! 

Participate in the SBCA Jingle Bell 5K

Put on your Santa hat, lace up those sneakers and get ready to run or walk for a great local school –South Boston Catholic Academy.  Stick around for a post-race party with prizes, raffles, food and fun! You can register here!  (Thursday is the last day to register online. You can register in person on Saturday)

Holiday Market at Snowport

Get in the holiday spirit! On Friday, the Holiday Market at Seaport will officially open!  The Seaport will once again transform into a magical winter destination with its third annual SNOWPORT, and the arrival of the first-ever The Holiday Market at SNOWPORT. The European-style, open air holiday market showcases over 60 small businesses, and will also feature a festive menu from Tuscan Kitchen and Breezy Hill Orchard, and enchanting holiday décor. The Holiday Market joins SNOWPORT in creating the ultimate holiday destination, complete with outdoor iceless curling, large-scale winter games, the Seaport Tree Market, and more!  You can get the details here!


The Bruins face off against the Lightings on Saturday at 7pm. The Celtics play the Jazz on Friday at 9pm and Saturday vs. the Trailblazers at 10pm. The Patriots face the Bills on MONDAY at 8:15pm.  Here are 10 Places to Watch the Game in Southie!



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