Things to Do in Boston in the Winter

igloos at envoy hotel boston,

While summer in Boston seems to fly by, winter in the city always drags, and when the temperatures outside aren’t conducive to long walks on the Charles River or a shopping stroll down Newbury Street, you can start to feel cooped up in your home. Luckily, there are a handful of activities that I love to do every winter which help to keep me sane!

If you’re looking for something different to do this winter, I’ve rounded up a few of my favorite activities to provide you with inspiration.

Do you have a top activity you like to do in Boston during the winter months? Please feel free to share!

igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the
igloos at the envoy hotel boston, the

The A-Lyst for Winter Activities in Boston 

Grab a Cocktail in an Igloo at LOOKOUT Rooftop + Bar

The heated igloos that take over the roof deck at the Envoy Hotel in Boston’s Seaport District each winter are quite the sight to see! Bundled up in your finest winter gear, you already feel like an eskimo, so on a cold winter night, why not hang out like one, too? Accommodating up to 10 people per igloo, the LOOKOUT Rooftop + Bar will keep you cozy with fleece blankets as they serve up a cocktails like the Senior Mint and Mulled Toddy– all you have to do is press a button for service! The igloos are open Wednesday – Saturday, 4 p.m. to 10 p.m. and given their popularity, I’d recommend going early. While the igloos have heaters, the rooftop itself is very windy and cold, so dress warm!

Ice Skate on Boston Common or City Hall Plaza 

What’s better than a little ice skating in the city, just in time for the Winter Olympics? Ice skating on Frog Pond in the Boston Common is a staple Boston activity during the winter months. Even though I am horrible on the ice, I love spending a weekend afternoon here attempting to live out my figure skating dreams. You pay $6.00 for admission and then can rent skates for $12.00 ($6.00 for children) and are able to spend as long or as little as you wish on the pond. Frog Pond is almost always busy and for a novice skater, like me, it’s a bit intimidating, so I was thrilled when another nearby skating rink opened! A few years ago, City Hall Plaza created “Boston Winter,” which features fun winter programming, including an ice skating path. For $15.00 + an $8.00 ice skate rental, you can take to the ice in the heart of Downtown Boston. For my fellow Instagram lovers, there’s an eye-catching Boston sign planted in the middle section of the rink, which offers the perfect backdrop for photos!

Drink Local Beer at the Trillium Garden at the Substation

Located in Roslindale, right outside of Boston proper, Trillium Brewery has created an indoor winter beer garden. If you visited the brewery’s widely popular outdoor beer garden on the Rose Fitzgerald Kennedy Greenway during the summer, think of this as the winter version! Serving a rotating 8-10 beers on draft, made locally in Canton, the pop-up allows you to bring in your own food to enjoy (they frequently have food trucks on-site, too!) for the ultimate weekend outing. If you’re looking for a fun group activity during the winter months, this is definitely it!

Test Your Puzzle-Solving Skills at Escape the Room 

Last March, my girlfriend organized a group to visit Escape the Room for her birthday, and it was a blast! After a boozy brunch, head over to Escape the Room’s nondescript location on West Street, and discover which one of your friends is the most observant, thoughtful, and strategic, as you try to “escape the room” in one hour. While the thought of being locked in a room is not exactly appealing, I promise it is not at all scary, and there’s even a panic button should you need a breather. The room is actually a puzzle and you and your friends have to solve it in order to escape. There are three room themes (we did “The Dig” and sadly, failed to beat it!), and you must really think outside the box – no pun intended – to get out. If you can organize 8-10 of your friends, this is a fun way to  spend a cold day indoors.

Be an Artist at the Saturday Open Studio in the Isabella Stewart Gardner Museum

Every Saturday, the Isabella Stewart Gardner Museum hosts a drop-in Open Studio, which is included in the price of admission ($15.00), inviting guests to create their own art. Hosted in the Bertucci Education Studio in the museum, no prior art experience is needed, and at the end of the session, guests take home their very own piece of artwork. Created as a way to inspire guests and further bring to life the beautiful work in the museum, class examples include portrait-making, marbling, and weaving. If you love the arts, this is a great way to get even more out of a winter weekend visit to this beautiful museum!

Ride the Musical Seasaws at Seaport Common

The Seaport District is hosting 15 illuminated musical seasaws this winter, kicking off on February 16. Free to use, these playground toys will be a seasonal fixture at Seaport Common, the green space located next to District Hall. The project is called Impulse and Boston is one of many cities to host the seasaws, which light up and play tunes as you ride them; the faster you ride, the brighter they will get! I mean, why wouldn’t you want to ride a glowing musical seasaw in 20 degree weather?!

Outfit Details:

Coat: LOFT Wool Jacket (similar here)

Sweater: J.Crew Tippi Sweater in Black

Jeans: J.Brand Maria High-Rise Jean

Hat: Black + White Pom Pom Hat (similar here)

Handbag: CHANEL Classic Flap in Black Caviar with Silver Hardware (similar here)

Photos by @KateSW

The A-Lyst is a Boston-based lifestyle blog curating the very best of style, beauty, food, and travel.