We all know Boston is known for baseball games at Fenway Park, lobster rolls, big universities, and the Boston Harbor Islands. Many of which are best enjoyed in the warmer months. But what about spending Christmas in Boston? Or spending the holiday time there in general leading up to Christmas? A festive Christmas tree, ice skating rink set against the backdrop of a beautiful city, and lights all aplenty. Christmas in Boston always delivers! Check out my top tips for you that will ensure your stay is magical.
Wear Warm Layers
It is no surprise that Boston being in the northeast area of the U.S. will be cold in November and December. Dress accordingly! Though the more recent winter seasons haven’t seen as much snow during the holidays, the temperatures still drop quite a bit. As you might expect from a city, there is lots of walking to do. So wear comfortable shoes or boots as well. New Englanders love their winter boots. In fact, they can be a bit of a fashion statement and are essential to staying warm and comfortable when the ground can gets a little wet from cold rain or snow. If you have a pair, be sure to pack them in your bag, because you’re going to need them for Christmas in Boston.
Purchase the CharlieCard
When traveling around Boston, you’ll most likely be using the “T”, the city’s subway system. It’s not called the subway or metro, so make sure you reference it as the “T” when asking locals about it. The CharlieCard is a contactless smart card used for fare payment for transportation in the Boston area. It is the primary payment method for the Massachusetts Bay Transportation Authority and several regional public transport systems in the U.S. state of Massachusetts. All you have to do is start with a small amount of money on the card. I suggest adding at least $20 to start if you plan on staying more than 3 nights. Another alternative is to use the ride sharing apps like Uber and Lyft, but they will be more expensive.
Check Out North End Neighborhood
The North End neighborhood is THAT quintessential neighborhood for exploring Boston. It is known for housing the Paul Revere statue and the Italian restaurants that make up “Little Italy.” Walking along the shops, you’ll see homemade pasta in the windows, and will smell the fresh seafood as you move from restaurant to restaurant. I don’t think you can go wrong with any restaurant here, but below is a list of some top favorites by locals:
- The Daily Catch
- Artu
- Antico Forno
- Mare Oyster Bar
- La Summa
Participate in SantaCon (Adults Only)
Looking for some fun adult time in the city? Check out the SantaCon crawl! Many cities in the U.S. organize this bar crawl where you can dress up in festive outfits like Santa, reindeer, and more. Another bar crawl opportunity is the Ugly Sweater crawl.
Enjoy Boston First Night
Boston First Night is an event that happens on New Year’s Eve in the city. This is essentially made up of a wide variety of different celebrations that occur in various locations! Throughout the day, you can find the city hosting a wide variety of fun activities such as performances, crafts, ice sculpture making, and more. Finish the night off with free fireworks over the water!
Stroll Down Beacon Hill
Beacon Hill is home to some of the most beautiful and quaint buildings in all of Boston. It’s often seen as one of the most picturesque parts of the city, and for good reason. Cobblestone streets in this area are lined by beautiful brownstones that Boston is most well-known for. During the Beacon Hill Holiday Stroll, visitors are welcome to walk through the neighborhood.
For more than 10 years, the Beacon Hill Business Association has sponsored a wonderful start to the Holiday Season. From 6:00 pm – 9:00 pm Charles Street is closed to traffic so that holiday shoppers and celebrants can stroll along the street and stop in to visit shops and offices and enjoy the refreshments laid out for them. Children start earlier with a visit to the Hill House fire house for free photos with Santa, and when the last picture is taken, Santa lights the business district’s Christmas Tree and officially kicks off the Holiday Season on Beacon Hill. Meanwhile, visitors enjoy Victorian carolers strolling among the crowds and take free rides in a horse drawn buggy.
Go Christmas Shopping
This is an obvious one, and also one not exclusive to Boston. However, there are SO many fun shopping experiences from both local artisan crafts in Quincy Market, to the modern fast fashion clothes you can find at the CambridgeSide Galleria Mall. There’s truly something for everyone. Another fun Christmas shopping experience is the Snowport Winter Village.
Snowport Winter Village
During the holiday season, The Boston Seaport is transformed into The Snowport Winter Village. The Holiday Market features 120+ makers, a tree market for all your evergreen needs, more food than ever before, with a custom cocktail bar from Tuscan Kitchen, and festive decor including a mistletoe arch, and winter wish wall. Hold on to your handwarmers — as Seaport turns into a giant snow globe and transformed the neighborhood into a magical winter getaway. Find gifts, treats, and plenty of surprises in this one-stop wonderland you can enjoy all season.
Go Ice Skating at Frog Pond
The Boston Common Frog Pond is home to a summer spray and splash pool in the summer and home to the outdoor winter ice skating place to be in Boston. Managed by The Skating Club of Boston® in a public-private partnership with the City of Boston. Year-round, family-friendly activities include the summer spray pool, historic carousel, winter ice skating, professional figure-skating shows, and special events for kids, families, citizens and visitors.
Watch the Boston Bruins play at TD Garden
TD Garden is home to both the Boston Bruins and Boston Celtics. Boston is a HUGE sports city and is home to 5 major sports leagues:
- Boston Patriots (NFL)
- Boston Red Sox (MLB)
- Boston Celtics (NBA)
- Boston Bruins (NHL)
- Boston Revolution (MLS)
But when thinking about Christmas in Boston, the quintessential game to visit is Boston Bruins. As you walk around the city, you’ll be hard-pressed to not find at least one person wearing the black and yellow jerseys.
Witness the Reenactment of Boston Tea Party
Every year, a group of locals put on a reenactment of the Boston Tea Party on December 16. That same day in 1773 was the day of the big event. Around 100 people help to reenact the event which is often watched by locals and tourists alike. This is a great way to learn more about Boston’s historical connections to America’s origins. One thing to note is that this does occur no matter the weather – rain, snow, or shine!
Watch the Santas in Speedos
You read that correctly! Santas in speedos. Who says Santa needs a big red coat and black boots to deliver the Christmas spirit? For Bostonians, nothing starts the season better than a scantily clad St. Nick braving the elements for the annual Santa Speedo Run. What began in 2000 as five guys spreading holiday cheer in Santa hats, beards, and Speedos, has grown to more than 700 men and women running to raise nearly $2 million for local children’s nonprofits including the Play Ball Foundation.
There are three ways to participate – 1) organize and fundraise for your own run; 2) join and fundraise for a run already in place; or 3) just simply make a donation, don your very own tiny red swimsuit (although some runners have traded those for wacky holiday costumes or matching zip-ups and joggers), and run roughly one mile somewhere in the Greater Boston area between December 4 through 12.
Check Out the Nutcracker Performance
Every year, the Boston Ballet puts on performances of the Nutcracker right around the holiday season. This truly is an iconic Christmas in Boston experience, even if you aren’t a big ballet fan. This classic story dates back to the early 19th century, and the performance by the Boston Ballet has broken numerous box office records. Similar to the Boston Pops, you’ll want to purchase your tickets well in advance as this is one of the most popular Christmas in Boston things to do!
Attend Faneuil Hall Tree Lighting
Though there are many different tree lightings throughout Boston for Christmas, none is as impressive as the Faneuil Hall Tree Lighting. This iconic celebration normally happens at the very beginning of December on a weeknight. Everyone gathers in the tiny cobblestone streets around Quincy Market to brave the cold and see the tree finally light up! This event is made even better because there are tons of fun celebratory performances from local bands and comedians up on stage. Be warned though: this event is very crowded.
Try to get there earlier if you want to be closer to the tree and the entertainment. Luckily, the tree is so large that you can see it no matter where you end up. Don’t forget to grab some local grub such as lobster rolls and clam chowder. An absolute must!
I hope you found my Christmas in Boston tips helpful! Please email me if you plan on traveling there and would like a vacation package with just a minimum deposit down. I can be reached at cassandra@accent-on-travel.net or feel free to fill out my contact form with your upcoming trip. BOOK YOUR BOSTON TOURS & EXCURSIONS WITH MY VIATOR AFFILIATE LINK!
Heading to Boston for a winter getaway after Christmas? Check out my feature in RedFin’s Top 10 Things to do in Boston in the winter.
Planning your Boston Getaway?
