Whether you’re eight or 80, Boston is especially enchanting come wintertime. For some, it’s the wonder of a first snowfall or ice skating surrounded by twinkling lights. For others, it’s the nature that’s distinctive in New England—tapping trees during maple sugaring season or taking a heated wildlife cruise to Boston Harbor Islands. Boston does the holiday season right, with tree lightings and festivals galore, and a cozy glow that blankets the city throughout all of winter. Each of the city’s 23 walkable neighborhoods is a playground for immersing yourself in sights, tastes, and experiences and creating new family memories together.
Wondering where to stay or when? Check out the fireplace rooms at the Newbury or other family-friendly hotels here, and subscribe to Meet Boston for ongoing updates on seasonal activities.
Go ice skating and eat at food halls
Boston offers the unparalleled thrill of skating in the great outdoors under glittering lights and a starry sky. Spots to lace up include Kirrane Rink in the Brookline neighborhood, Kelly Skating Rink in Jamaica Plain, and South Plaza in Cambridge. Among the most iconic is Boston Common Frog Pond, an ideal jumping-off point for adventures in the city center. From there, Beacon Hill’s charming paths, illuminated by gaslights, await—along with one of the city’s most family-friendly independent bookstores. Get hot cocoa at Beacon Hill Books & Cafe with its children’s corners featuring Harry Potter and interactive train displays.
When one kid wants meatballs, the other insists on grilled cheese, and adults prefer something local and seasonal, choose among multiple crowd-pleasing options. Three of Boston’s food halls—Time Out Market, High Street Place, and Boston Public Market—are family- and wallet-friendly ways to enjoy a smorgasbord of on-the-go comfort food with everything from New England lobster rolls to cider donuts. Entertainment at Boston Public Market is free each Saturday with drop-in kids’ craft events and Sunday sing-alongs with a guitarist.
Celebrate the holidays outdoors in Boston
One of Boston’s most beloved winter festivities is the annual tree lighting in the Faneuil Hall Marketplace and Quincy Market.
Courtesy of Meet Boston/Kyle Klein
The entire city of Boston comes aglow starting in November—and the entire family can enjoy some of the more notable tree lightings, including historic Faneuil Hall Marketplace (grab a cocoa or balloon animal before holiday shopping). Victorian-era brownstone homes make an excellent backdrop for a family selfie on Boston’s holiday lights trail, which takes you to some of the city’s most festive displays on foot. Those with little ones may also want to hop on and off Old Town Trolley Tours’ Holiday Lights and Sights experience—and, if you’re there on a Saturday, stop at Boston Common for the early show of a holiday-themed illuminated drone performance orchestrated to music.
Sports-loving families won’t want to miss out on a Celtics basketball game or a chance to catch the Bruins on the ice—and they can also test their prowess with curling. The Canadian pastime is one of the highlights of the Snowport pop-up village.
Snowport pop-up winter village in the Seaport District features more than 100 craft vendors, fun foods, and winter sports like curling.
Courtesy of Meet Boston/Alexander Pickering
The event transforms Boston’s Seaport District into a glowing open-air holiday market each holiday season, featuring tasty treats, music, and the mascot Betty the Yeti. She’s furry, friendly, and ready to take pictures with kids of all ages. Another festive pop-up village, Winter Fest in Charlestown, also returns this year, bringing après ski vibes, a pop-up outdoor rink, and Santa’s workshop with crafts and picture opportunities.
For culture fans, a theater experience is a memorable choice while they’re in town. There are several Nutcracker performances from which to choose (Boston Ballet’s is world-famous), or check out symphony performances with the Boston Pops orchestra or the annual Black Nativity stage run.
Ring in the new year with fireworks, art shows, and a nature cruise
Copley Plaza is one of Boston’s most popular spots to gather for New Year’s Eve fireworks.
Courtesy of Meet Boston/Kyle Klein
New Year’s Eve in Boston, known as First Night, is an all-day affair that’s perfect for families. The fun starts the morning of December 31 with free rides on the Rose Kennedy Greenway Carousel (which operates all winter long). Festivities also include a parade, a puppet show, an ice-skating show on Frog Pond, and a mini fireworks display on Boston Common at 7 p.m. Plus, kids can marvel at ice sculptors as they create their works of art at City Hall Plaza and along a waterfront trail.
Depending on the weather, these sculptures can last for weeks into the new year. (Check Meet Boston for ongoing seasonal updates.) That’s just about the time that the Winteractive art walk kicks off with gigantic, interactive play elements at 17 sites throughout the city, including near the New England Aquarium and in Downtown Crossing’s pedestrian-friendly thoroughfares.
Of Boston’s many charms, one of the best is the city’s proximity to nature. Enjoy it with events, such as a heated boat excursion offered by the National Park Service and the aquarium. The annual winter wildlife cruise brings families up close and personal to the seals and owls around the Boston Harbor Islands, which you can only see once the mercury dips.
Go sledding and attend Lunar New Year in the center of Boston
Chinatown comes alive with music, dancing, costumes, and revelry during Lunar New Year parades.
Courtesy of Meet Boston/Jessica Mading
Boston’s thrills include sledding in the center of the city during the Children’s Winter Festival. Each February, Boston Common hosts a 45-foot-long toboggan slide and outdoor games like inflatable Skee-ball.
Big fun comes in small packages at the annual model ship show at the USS Constitution. The world’s oldest commissioned naval warship that’s still afloat, it’s the showpiece of Charlestown, and its three masts tower over the neighborhood, inviting visitors aboard. Ship admission is free year-round, while the February exhibition of miniatures at the USS Constitution Museum is by donation.
Families can celebrate Lunar New Year, one of Boston’s most immersive winter events, and see the vibrant gold, red, and yellow decorations. (In 2026, it takes place on February 17; subscribe to Meet Boston for more info.) Festivities kick off in the heart of Chinatown with a cultural village featuring arts and crafts for kids, calligraphy, and musical performances. It’s all capped off with a parade and joyous lion dance through the streets, the sounds of drums and clapping echoing through one of Boston’s most historic neighborhoods.
Boston’s Chinatown
Courtesy of Meet Boston/Kyle Klein
Family-owned restaurants line the streets of Chinatown, where culinary experiences, such as dim sum, await. The shared small plates are ideal for adventurous eaters, with steamed dumplings and bao buns pleasing just about every palate. Afterwards, hit up the Chin Park PlayCubes.
One of New England’s most delightful natural phenomena comes each February and early March during freezing and thawing cycles. It’s then that sap starts flowing from the maple trees blanketing Mass Audubon in Mattapan, and families can learn more about how syrup is made during a storybook walk and a scavenger hunt. (Since syrup season is highly dependent on nature’s whims, check the Audubon’s schedule for ongoing updates.)
Whether it’s touching snow for the first time, the scent of cocoa in the air, or seeing historic cobblestone streets aglow, winter offers singular delights for young and old in Boston. Subscribe to Meet Boston for ongoing updates on what to see, eat, do, and how to immerse yourself in it all.
