South Boston Catholic Academy’s 13th Annual Jingle Bell Run

South Boston Catholic Academy 866 East Broadway, South Boston , United States

Register now for South Boston Catholic Academy's 13th Annual Jingle Bell Run!  The race will be held on December 3rd and the Youth Races will being at 9 AM while [...]

$30

South End Holiday Stroll

South End Boston Washington St., Boston, MA, United States

Come celebrate the holidays in the South End! The South End Business Alliance (SEBA) is sponsoring the annual South End Holiday Stroll with events scheduled for Saturday and Sunday, December [...]

Love Child’s Espresso Martini Festival

Love Child 364 W Broadway, Boston, MA, United States

The name says it all! AN ESPRESSO MARTINI FESTIVAL. WE REPEAT AN ESPRESSO MARTINI FESTIVAL. Love Child has had the idea to host a fun tasting festival since they secured [...]

Seaport Tree Market

Boston Seaport 60 Seaport Blvd., Boston, MA, United States

That fresh evergreen scent, no saw required. The Tree Market at Seaport has your holiday decor covered with a selection of trees, wreaths, lights and more. The best part? Evergreen [...]

City Tap House’s Annual Pancakes and Pajamas Brunch

City Tap House 10 Boston Wharf Rd, Boston, MA, United States

It's back! Grab your FLIPPIN’ jammies because on Saturday, it’s on at City Tap House's annual “Pancakes & Pajamas” brunch! ⁠Brunch will be held on 12/10, from 11am-3pm⁠.  Pancake specials include: [...]

1st Annual Cisco Stroll

Loco 412 W Broadway, South Boston, MA, United States

Get dressed in your holiday best Saturday, December 10, because Cisco Brewers is serving up their Nantucket Stroll tradition at five of your favorite Southie bars. Cisco Stroll has it [...]

Ugly Sweater Bar Crawl

Wild Rover 61-63 Chatham St., Boston, MA, United States

Are you feeling blessed and Christmas sweater-obsessed, Boston? Head to the back of your Grandma's closet and grab the ugliest and most hilarious holiday sweater, because we’re taking the city [...]

Kickoff for Kids’ Bowling with Santa

South Boston Candlepin 543 E Broadway, Boston, MA, United States

Bring your kids to go bowling with Santa Claus on December 11th!  There will also be pizza, goodie bags, and a free photo op with Santa himself!

Todd Snyder Opening

Seaport Common 85 Northern Ave., Boston, MA, United States

Join Todd Snyder at The Superette in Boston Seaport for their opening on Monday, December 12. Shop their signature essentials, statement pieces, custom suiting, and iconic accessories reflective of quintessential [...]

Gray’s Hall Toy Drive

Gray's Hall 615 E Broadway, Boston, MA, United States

This Wednesday, 12/14, Gray's Hall is hosting their annual Troy Drive for their friends at @sbnhtheollie 🙌🏼 If you are feeling fortunate this year, bring an unwrapped present and get [...]

Wreath Making at Castle Island Brewing Co.

Castle Island Brewing Co 10 Old Colony Ave., South Boston, MA, United States

Bring your friends and join us at Castle Island Brewing Co. in decorating a wreath for you to proudly display during the festive season in the back room in Southie! [...]

Sip & Shop Showcase at The Broadway

The Broadway 726 East Broadway, South Boston, MA, United States

What better way to cross off your holiday shopping than supporting local small businesses + sipping on a delicious cocktail all in ONE place! Join The Broadway on Wednesday, December [...]