Christmas lights and snow in Boston

With its annual coating of snow, revolutionary-age redbrick buildings, and historic local culture—Boston, Massachusetts is a special place to celebrate the holidays. We have local events that accentuate the city’s festive spirit, brilliant shopping markets in the most bustling local destinations, and romantic experiences like ice skating and musical experiences. 

For some more specific examples to guide your upcoming visit, check out this guide on how Boston does the holidays. 

Dashin’ Through The Bars

December 14th 

Bostonians enjoy a good party, and if you want to tap into that local culture during the month of December, there are few better options than Dashin’ Through the Bars. The annual pub crawl is a popular and joyous event for locals and travelers alike. Whether it be an ugly sweater, full-on Santa suit, elf costume, or a childlike holiday onesie—you’re encouraged to wear your favorite holiday attire to the event. 

The marathon of a party will begin at 2pm on December 14th, and run all the way until 10pm. The crawl will begin at the beloved and historic Finn McCool’s on HIgh Street, and there will be a second registration at 4pm at High Street’s Howl at The Moon. Other participating venues include Wild Rover, Sissy K’s and Blackstone Grill. 

Dashin’ Through The Bars. Boston, MA

Shopping at Faneuil Hall

Faneuil Hall Marketplace is a historic shopping center a five-minute walk from The Boxer Boston Hotel near downtown. In addition to its three historic market buildings, and the promenade that’s constantly bustling with vendors and street performers—Faneuil Hall is also home to one of the city’s most well-curated holiday markets. 

Travelers czming through Boston this December can stop by Faneuil Hall on any day to browse shops for local gifts. There will also be holiday tree sound and light shows here throughout December, Holiday Pop-Up sales, photo opportunities with Santa Clause, and a whole lot more.

Faneuil Hall. Boston, MA 

Skating on The Common

Located in the heart of Downtown Boston, The Boston Common is the country’s oldest public park and a romantic destination unlike any other. You can find a well-lit Christmas tree here throughout the month of December, and you can find one of the most romantic holiday season activities Boston has to offer—ice skating on the Frog Pond. 

Every year, this historic area of the park gets a frozen makeover with skate rentals available for everyone in the family. Adults can pick up a pair of skates for just $12 here, and kids can rent for just $6 a pair. Check out The Boston Common Frog Pond website to discover hours and accompanying attractions at this year’s ice skating rink. 

The Boston Common Frog Pond. Boston, MA 

The Holiday Pops

December 15th-21st 

The Boston Pops Orchestra is an iconic Boston-based orchestra that specializes in popular sounds of the symphony. It serves as the central performance group for a number of beloved local traditions including the annual 4th of July Boston Fireworks Show, and the annual run of Holiday Pops shows. These festive performances began in 1973 with former conductor Arthur Fiedler. 

This December, the tradition will continue for a series of magical nights at Symphony Hall. The show will consist of holiday musical classic after classic, with a traditional Pops sing-along, and a special visit from Santa Claus. 

Boston Symphony Hall. Boston, MA 


Planning a visit to Boston? Experience it like a local with our insider’s guide at the Boxer Boston blog!