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The best things to do in Boston this weekend

Find the very best things to do in Boston this weekend including cool events, lively shows and so much more

By Eric Grossman and Time Out Boston Staff |
Boston waterfront
Photograph: Shutterstock

It’s 2020 and Winter is in full force, but that doesn’t mean you have to stay inside—just check out our list of the best winter activities in Boston. The Hubs cultural calendar is relentless this time of year; at any given time, there are plenty of noteworthy shows and events taking place across the Hub. If nothing on our list here strikes your fancy, take a look at our guides to the best places to see live music, best cheap things to do, and best free things to do in Boston. If you're looking to get out of the elements, consult our guide to where to see art in Boston, including the best art galleries and best museums in Boston.

RECOMMENDED: Full guide to the best things to do in Boston

The best of the city under one roof

Time Out Market Boston
Photograph: Eva Sakellarides

Check out the action at Time Out Market Boston


Boston’s newest destination for all things food and drink has burst on to the scene, attracting hordes of ravenous foodies and a diverse mix of locals and visitors to its jaw-dropping home at 401 Park in the Fenway. Keep an eye on the @timeoutmarketboston IG handle for specific events, including DJs (every Fri and Sat from 7-10pm) and live jazz (most Sundays from 11am-1pm). Before (or after) your next visit to Time Out Market, enjoy a spin on the brand new Rink at 401 Park

Things to do in Boston this weekend

Photograph: Courtesy ICA Boston
Museums, Art and design

Kusama’s LOVE IS CALLING at the ICA

Seaport District

Be among the first wave to come and experience the new anchor of the ICA Boston’s collection. LOVE IS CALLING (2013) is the largest and most immersive of the iconic Japanese contemporary artist Yayoi Kusama’s Infinity Mirror Rooms, which have thrilled museumgoers across the globe. Visitors enter a darkened, mirrored room illuminated by inflatable, tentacle-like forms—covered in the artist’s signature polka dots—that extend from the floor and ceiling, gradually changing colors. The installation is accompanied by a continuous recording of Kusama reciting a love poem in Japanese.

Boston Wine Festival
Photograph: Courtesy Boston Wine Festival

Boston Wine Festival at the Boston Harbor Hotel


The Boston Harbor Hotel presents the 31st annual Boston Wine Festival—the nation’s longest-running wine and food pairing series—through late March. Executive Chef Daniel Bruce and the hotel have invited renowned winemakers from around the world to participate; the public can choose from numerous seminars and themed dinners, and there's also Uncorked for a Cause on Feb 28 (an evening partnering with Share our Strength to benefit the No Kid Hungry campaign).

Photograph: Courtesy Yelp/BCAC
Theater, Performing arts space

We All Fall Down at the Calderwood

South End

Running through Feb 15, Huntington Theatre Company at the Calderwood Pavilion at the BCA presents We All Fall Down, a new comedic play by Huntington Playwriting Fellow (and Somerville resident) Lila Rose Kaplan.

The Wilbur Theatre, Music and nightlife, Boston
Photograph: Jessica Howe
Music, Music venues

Nikki Glaser at The Wilbur

Theater District

Nikki Glaser plays a pair of shows on Jan 24 at The Wilbur. The comedic powerhouse will bare all, sharing her personal stories and treating crowds to numerous "did she just say that?" moments.

Boston Common Frog Pond
Photograph: Shutterstock/Kwanbenz
Things to do

The best ice skating in Boston

Wintry weather means it's time for ice skating in Boston. Here are our picks for the best places for lacing up some skates and taking a spin around the ice.