Five Fun Boston-Area Family Winter Activities

Mother and father hold their smiling 5 year old son's hands and walk down a cobblestone street in Boston's Beacon Hill; they're in winter coats and it's snowing, a light layer of white coats the street.

Stuck in the New England doldrums of mud, freezing rain, and occasional snowstorms? Watching your kids run around the house, seemingly done with their holiday presents already? There’s no reason to start counting the days until April: we can all keep having fun this gloomy season, I promise. Here are my top recommendations for winter family activities in Boston.

Five Fun Family Things to Do In The Boston-Area This Winter

4 year old boy, seen from behind as he splashes along the beach in bright yellow rain boots and a forest green winter coat. There is a wall of white fog ahead of him.


Head to the Beach

My favorites are Wingaersheek and Crane! Hear me out: no one is at these beaches in the wintertime besides a few dog-walkers, the parking is easy, and the landscape is full of amazing things to discover. There are tide pools, shells, rocks to climb, flotsam and jetsam, a faraway lighthouse, bewildered birds … what more could a family need? Bring a kite. Bring a waterproof picnic blanket. For Crane, consider walking the gardens at the estate as well. For Wingaersheek, bring some sweets from Nichols Candies, or warm drinks from nearby Cape Ann Coffees.

It will be grey and windy and no matter your kid’s age, they will be delighted to be there.


Mother and 1 year old daughter sitting in windowseat of Beacon Hill Books; she is wearing a bright pink dress and smiling as her daughter examines a toy.

Peruse Books, Get Hot Cocoa

Porter Square Books in Cambridge has a well-curated children’s section and comes with the attached delicious Cafe Zing. Further down Mass Ave, Harvard Book Store benefits from being near Burdick’s for the most luxurious hot chocolate ever, Cardullo’s for candies and chocolates from around the world, Tatte for a croissant or sandwich, and plenty of nearby places for pizza, burgers, or burritos.

In Boston, Beacon Hill Books has possibly the most adorable children’s section you’ve ever seen, plus a downstairs cafe. Plus, it’s in Beacon Hill, so no matter the weather is like you will feel like you’re walking in a Charles Dickens novel.


3 year old boy in a blue knit hat and white sweater runs toward his mother's outstretched arms, his eyes closed.

Go on a Winter Hike

Bundle up and check out Broadmoor in Natick for long boardwalks over marshland with benches that are perfect for sitting and snacking, a little rocky climbing area, lots of bird-watching opportunities, paths through the woods, and the highest percentage of friendly strangers I’ve found.

Habitat in Belmont is a shorter walk with lots of fun surprises: diverging paths through meadows or around ponds, the tallest pine trees I’ve seen, seasonal goats, owls swooping around dusk, and one path with little boxes that strangers hide pine cones, special rocks, or the occasional dollar bill inside. There’s something peaceful and lovely about Habitat all year.


Black and white image of three young brothers play in their Belmont MA backyard, throwing leaves at each other and laughing

Wander a Less Populated Grown-Up Museum

The truth is that mostly kids just want to explore, and every museum is great place to do that. Many of the amazing museums that Boston has to offer are far less crowded than the ones made for children.

The Harvard Museum of Natural History in Cambridge has an incredible, admirably nauseating collection of jarred insects, as well as an amazing rocks and minerals room, a two-floored room of taxidermied animals including suspended whale skeleton, and the famous glass flowers that many people seem to admire but I struggle to enjoy. I keep meaning to do all of my holiday shopping exclusively at their gift store because it is great.

The Isabella Stewart Gardner Museum is basically a castle with a gorgeous indoor courtyard, plus it has an unsolved mystery. Fun for the whole family!

And if you’re willing to make a bit of a drive, Mass MoCa in North Adams is basically a massive kids and adult playground, housed in a former warehouse. Much of its artwork is interactive and multimedia, including interesting sound effects through skyways, moving light patterns projected on sculptures, and a room full of instruments you can play. The last time we went an artist had installed a roller coaster that you could actually ride. Get an airbnb or spend the night across the street at Porches for a fun family art slumber party.


Blonde mother in a tan camel hair coat holds her toddler son close; they are smiling and touching noses, evergreens behind them.

Be Warm and Surrounded By Green

At some point in winter I start to feel a little broken in my brain and the only cure for it is to be surrounded by greenery and warm, humid temperatures. Enter the butterfly garden in the Boston Science Museum: you can sit on a bench in there as long as you like, watching the butterflies languidly wander through the air and examining all kinds of interesting creatures on your way out.

The Lyman Estate Greenhouses are also green and warm and historic and delightful (although note: the narrow gravel paths have a few steps and are not particularly stroller-friendly, so if you have someone under 2 with you, you’ll want to carry or wear them).

The New England Botanic Garden has the balmy Orangerie and the cooler-but-still-pleasant Limonaia: two places I am super excited to check out this winter for some indoor greenery and interesting architecture!



Family Winter Activities Around Boston

Here’s a life hack: many of these Boston family winter activity ideas make super fun winter photo session ideas too! Get in touch with me today to get some suggestions tailored to you and schedule your maternity, newborn, milestone, or family session.

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