A Local’s Guide to Everything on Boston’s Freedom Trail
Boston is a city teeming with history around nearly every corner. While this city built on Massachusetts Bay is chock full of unique…
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Boston in the wintertime is a scene straight out of a storybook: blankets of freshly-fallen snow, locals bundled-up in heavy coats and colorful scarves, and historic charm aplenty. And fortunately, the city really leans into all aspects of the holiday season, with plenty of activities and experiences that are designed to get locals and visitors alike into the spirit.
Check out some of the best ways to celebrate the magic, mistletoe, and merriment of this special time of year.
Boston Common tree lighting
While there are several different tree lighting events throughout the city and throughout the season, the most notable is Boston Common’s event, which usually takes place in late November or early December.
It features a great lineup of live entertainment, delicious food and beverages from local vendors, and of course, the exciting illumination that signals the start of the holiday season — the annual tree is a gift from Nova Scotia as a token of gratitude for the city’s help during the Halifax Explosion in 1917.
When: 6-8 p.m. Thursday, Nov. 30, 2023
Copley Square Christmas tree lighting
Just a short walk away from the common, Back Bay’s Copley Square has a popular annual tree lighting ceremony as well.
Though it’s smaller scale, you’ll enjoy performances by the Boston Pops Esplanade Brass Ensemble, the Boston Children’s Chorus, and singer Ackeem Hill, plus visits from Santa Claus and Rudolph and food and refreshments from Dunkin’, H.P. Hood, and Drake’s Cake’s.
When: 5-6 p.m. Monday, Nov. 27, 2023
Faneuil Hall tree lighting
The earliest of the tree lighting ceremonies in town, Faneuil Hall gets into the spirit around Thanksgiving every year. While its iconic Blink! show, which sets festive lights to music, is unfortunately no longer around, there will still be a lit tree perfect for holiday photo ops that adds a fun touch to your Christmas shopping.
When: 4-7 p.m. Tuesday, Nov. 21, 2023
Christopher Columbus Park trellis lighting
Looking for a particularly romantic holiday outing? Sneak a smooch underneath the twinkle lights of the gorgeous trellis at Christopher Columbus Park as you walk along the waterfront.
When: 5 p.m. Monday, Nov. 20, 2023
The Boston Ballet’s “Nutcracker”
If there’s no “Nutcracker” performance, is it even Christmas? The Boston Ballet puts on an incredible retelling each year of this timeless story.
The sets are lavish, the music is thrilling, and the dancers’ skill is undeniable. It’s hard not to fall for the magic of the waltzing flowers and glittering snow as you follow Clara on her journey through the Kingdom of Sweets.
There are plenty of shows from late November to the end of December, so you can find a time to relive the magic.
When: Nov. 24-Dec. 31, 2023
Holiday Pops concert at Symphony Hall
This is truly a classic Boston experience. Every year, we Bostonians gather at Symphony Hall to listen to Christmas music performed by the Boston Pops Orchestra and led by beloved conductor Keith Lockhart. There’s an appearance by the man in red, of course, the musicians put a little swing into their show, and it’s all around festive good fun.
Holiday Pops is popular, so claim your preferred date early. There are concerts throughout December, starting early in the month. They have a kids matinee and even a sensory-friendly concert.
Hanukkah: The Festival of Lights
The Museum of Fine Arts Boston hosts an annual festival including not just visual art but also performances, crafts, and programming to engage all ages.
Previous years have included make-and-take art, a taste of classic dishes like latkes and rugelach, Hanukkah songs performed in Yiddish, Hebrew, Ladino, and English, and a community candle lighting.
First Night
The city’s long-running New Year’s Eve celebration — the first and oldest in the entire country! — First Night is a family-friendly outdoor event that features live entertainment, food, and drink, plus beautiful ice sculptures for attendees to marvel at. Just be sure to bundle up, as most of the activities are outdoors!
This year’s celebration includes performances from dance academies, classical music ensembles, and puppet theaters.
When: 10 a.m.-midnight Saturday, Dec. 31, 2023
Sledding
It’s one of the most beloved winter pastimes, and for many kids (and the young at heart), it’s just not quite a snow day without it. Flagstaff Hill in Boston Common will do in a pinch if you find yourself in the heart of the city, but for truly superior sledding spots, you’ll need to venture out of town a bit.
Top tobogganing picks in the area are Danehy Park in Cambridge, Larz Anderson Park in Waltham, and Corey Hill Park in Brookline.
Ice skating
There’s plenty of family-friendly fun to be found at the Frog Pond in Boston Common, which transforms every winter from a splash pad and wading pool into a bustling rink that could fit right into a Hallmark movie.
The admission price is based on your height — free for those under 58 inches, $8 for those 58 inches and over, You’re free to bring your own skates or rent a pair ($10 for kids, $15 for adults). And before or after you show off your skills, warm up with a coffee, hot cocoa, or a treat from the on-site snack bar.
Boston Christmas markets and shopping
Looking for a unique and memorable gift for your friends, family, or sweetheart? There are plenty of festive annual events that will help you knock some presents off of your shopping list and get you into the holiday spirit.
- Snowport is a full-on winter wonderland at the Seaport — complete with curling!
- The SoWa Winter Festival features food trucks, live ice sculpting, and a marketplace of artisans and vendors.
- Christmas in Boston, a shop open all year-round in Faneuil Hall, is chock-full of ornaments, trees, home decor, and good cheer.
Cocoa and cocktails
Of course, you can only wander around in the chilly Boston winter weather for so long before you need to warm up. And there are plenty of spots to do just that — L.A. Burdick Chocolates, with locations in Back Bay and Harvard Square in Cambridge, makes some of the richest, most delectable hot chocolate around.
Pro tip: Get the small unless you’re planning to share.
Over at the Boston Public Library, the Map Room Tea Lounge offers both a traditional tea service and tea-inspired cocktails, like the TCA Manhattan, with bourbon, housemade jasmine and black tea vermouth, and angostura bitters, and the Perfect Pair, featuring housemade matcha liquor, matcha powder, and coconut creme. It’s the ideal spot to bring your haul of library books and read the afternoon away.
For an extra-special experience that takes the chill out of your bones and satisfies your appetite, seek out one of the Boston restaurants with a fireplace. These include:
And just about every restaurant and bar in town has seasonal cocktails that will have you feeling cozier in no time. One of the most well-known is the Tom & Jerry at No. 9 Park, a hot, eggnog-like concoction that has a loyal legion of fans — but the caveat is that it’s only served when it’s snowing, and the snow sticks, between Nov. 1 and Feb. 13.
But fortunately, there are other seasonal options not contingent on precipitation:
- An herbal hot toddy at Stillwater
- Mulled wine at Capo
- The “Ole Man Winter” with vanilla vodka, hazelnut liqueur, and coffee, at Bowery Bar
Boston walking tour for the holidays
If you’re in town for the holidays and it’s your first visit to Boston, get acquainted with a walking tour of Freedom Trail. Highlights include Faneuil Hall (where you’ll see the Christmas tree). the Old State House, Old South Meeting House, and Scott Alley, one of the oldest and narrowest streets in Boston.
If you don’t mind colder temperatures, the holiday season can be a wonderfully charming time to experience the city at its quaintest and coziest. Just make sure you bring a warm winter coat!
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