The best things to do in Boston this weekend: Dec. 19–22

Pregame the holidays with brunch, get last-minute shopping done and more.
The architecture of Boston in Massachusetts, USA at night showcasing the Boston Harbor and Financial District with its mix of contemporary and historic buildings.
Photograph: Shutterstock / Marcio Jose Bastos Silva
Edited by Jacqueline Cain in association with Capital One
Advertising

For those of us not getting out of the city ahead of the holidays, it'll be a fun weekend in Boston. You could check out a pop-up maker market and an iconic light display—and read on for more. Our on-the-ground editor and writers traverse the metro area looking for the best of the best things to do, updated each week.

RECOMMENDED: Full guide to the best things to do in Boston

Time Out Market Boston

Alongside the usual major lineup of food vendorssatisfying comfort food and seasonal cocktails, there are new Nutcracker-themed drinks especially for December. And showcasing the best of the city always goes beyond just food and drink with frequent events. This weekend, live DJs are on the decks spinning seaonal jams both Friday and Saturday nights. On Saturday, Dec. 21, the pop divas don their holiday best for Sleigh All Day: Drag Brunch & Bingo. Enjoy brunch specials from vendors and the show between 1–2:30pm. Plus: December 22 is the latest Swiftie Sunday, Time Out Market's monthly celebration of all things Taylor. Beginning at 5pm, dance to Taylor’s hits with a live DJ spinning 'til 8pm and sip on themed cocktails, available til 10pm. Dress up as your favorite era for a chance to win a gift card to use around the market.

Things to do in Boston this weekend

  • Breweries
  • Kendall Sq
  • price 2 of 4
  • 5 out of 5 stars
  • Recommended

The time has come to bid adieu to Cambridge Brewing Company in Kendall Square, which will close after service on Friday, Dec. 20, after 35 years. But wait! This isn't goodbye forever to some of our favorite CBC beers. Castle Island Brewing Co. announced today that it will continue to produce lables like Cambridge Amber and Flower Child IPA, and make them available at its Southie and Norwood taprooms, as well other restaurants in the area (and hopefully, retail stores to come). As I chronicled in an oral history story in 2019, Cambridge Brewing Company had an outsize impact on Boston's beer scene—so this community continuation of the beloved brand doesn't surprise me, but it does delight me. Cheers, CBC and CIBC!

https://media.timeout.com/images/106204282/image.jpg
Jacqueline Cain
Editor, Time Out Boston

This pocket-sized "adult snack bar" from celeb chef Tiffani Faison’s Big Heart Hospitality Group is the latest bar to get all dolled up for the holiday season. Fool's Errand is always ornamental, with crystal chandeliers and irreverent French wallpaper. But the blue-and-white Fenway jewel box gets a glow-up in December with twinkling lights and snowflakes on the ceiling. Enjoy the atmosphere while sipping on one of the "Foolish Cocktails," like "I Saw Dad Kissing Santa," with vodka, pomegranate, apple, lemon and allspice dram; or Fireside Indulgence, a mug of hot chocolate with bourbon and toasted marshmallow Fluff.

  • Cafés
  • Downtown

L.A. Burdick Chocolates has opened its third Boston-area location in Coolidge CornerThe full-service café and retail counter has an expansive retail selection from the famed New Hampshire makers of exquisite chocolate bonbons and delicious drinking chocolate, including gifts for chocolate lovers as well as the artisan company's full range of treats. It also offers counter and table service for a menu of chocolate bonbons, pastries, cookies and beverages—hopefully staving off the hanger of any last-minute shoppers.

  • Things to do
  • East Cambridge

Earlier this year, chef Will Gilson and his Cambridge hospitality group opened two new spots on First Street: all-day café and rotisserie Amba, and a next-door farmers market and events space, First Street Market. The latter is inaugurating its first holiday season with a series of maker markets. The in-house bar will be open with libations to fuel this weekend's festivities, which continue from 5–9pm on Friday, Dec. 20, and from 11am–3pm on Saturday, Dec. 21.

  • Things to do
  • Seaport District

If singing loud for all to hear is your idea of a good time, head to the Seaport cinema for an Elf movie party on Sunday. (Sick of Elf? See what's playing elsewhere at Boston's best movie theaters.) On December 22, Alamo Drafthouse hosts a sugar-fueled screening of the holiday classic—one of the Time Out global film critics' top picks for Christmas flicks—beginning at noon. Alongside the full food menu and specials inspired by Elf, Alamo is throwing in festive games and interactive props (including personal elf hats), with caroling, and quoting, encouraged.

  • Things to do
  • Markets and fairs
  • South End

The SoWa Winter Festival has been open every day since Black Friday, for the first time in the South End tradition's 10-year history. So hopefully you've already completed your shopping! But if you still need something from the expansive maker marketplace—or the Food Truck Village—now's your final chance. SoWa Winter Festival season ends Sunday, Dec. 22. Until then, it's open at 4pm on weekdays and 10am on weekends, closing at 8pm Thursday, 9pm Friday and Saturday, and 7pm on Sunday. Food trucks roll up Friday from 5–8pm, Saturday from 12–6pm and Sunday from 12–4pm.

  • Things to do
  • Festivals
  • Charlestown

Can’t get enough holiday wonder? Winter Fest is just what you need. From the creative minds behind Boston’s Wicked Haunt Fest, Winter Fest at Hood Park in Charlestown is a winter wonderland filled with massive light displays and family-friendly holiday magic—here's a look. Visitors can meet Santa on weekends and see a life-size gingerbread house and toy workshop. For adults, the Après Ski Veuve Clicquot Gondola Lounge transports guests to Aspen for a champagne toast. Look for treats like decadent hot chocolate adorned with seasonal toppings like house-made marshmallow and crushed peppermint. Beer and wine is also be available. It's free to attend, though food, drink, skating and meeting Santa incur charges from $10–$30.

  • Things to do
  • Ice skating
  • Boston Common

This weekend is will be brisk, but if you clutch a hot drink with your mittens, it can be charming. One of the best winter activities—which isn't dependent on snow—is hitting an ice rink. Boston and the surrounding area has no shortage of rinks fit for all levels, but none are as iconic as the Boston Common Frog Pond. Situated on the oldest public park in America, the rink hosts a steady, multigenerational throng of newbies and aspiring Kristi Yamaguchis alike. (Those who prefer to stay on non-slippery ground can snuggle up beside the snack bar with a hot chocolate and free Wi-Fi.) Just be sure to bundle up—a wait is inevitable.

  • East Cambridge

Wish you could eat at Boston’s best restaurants all in one sitting? Geppetto has you covered this holiday season with their 12 Chefs of Christmas events. Every Sunday this December, chef-owner Will Gilson is inviting over some of greater Boston’s top culinary talents to create curated, coursed meals showcasing their favorite flavors and festive takes on holiday dining. This Sunday, Dec. 22, is a dinner party with Joey Gonzales of Amba Alexis Babineau, Puritan & Co. Hal Ryerson of the Sweet Life on Martha's Vineyard, and Andre Lacroix of Herb Lyceum in Groton. You must book for this event in advance, and it will be $110 per person.

More things to do around Boston

  • Things to do
The 50 best things to do in Boston
The 50 best things to do in Boston

No matter where your interests lie, you can always find something to get excited about in the Hub. The best things to do in Boston run the gamut—from seriously fun to awesomely educational.

Need somewhere to stay?

Recommended
    You may also like
    You may also like
    Advertising