How to Spend a Cold Day in Boston [02/19/24]

There are so many cool things going on in Boston this season. From winter dining experiences to outdoor skating rinks, there’s never a dull moment here in The Hub. But having a memorable evening isn’t just about popping into an event, it’s about creating a truly Boston experience.

We’ve put together three itineraries for you to maximize a wintry day in the city. Everything is all planned, all you have to do is go!

by Celina Colby

DATE NIGHT

First - Start your evening by snow tubing at the Harpoon Brewery Slopeslide in Seaport. This is snow tubing in the city and it’s a nostalgic blast from the past. Race down the man-made hill on a cushy LL Bean snow tube, then toast a successful run with a Harpoon beer.

$10 for one hour | Take the Silver Line to Northern Ave at Harbor Street

Next - Walk 13 minutes to Borrachito Taqueria, a delicious taco spot with a chic speakeasy hidden in the back behind a freezer door. Sip Instagram-friendly craft cocktails and enjoy a wide variety of tacos all served up on homemade corn tortillas.

Price varies | Walk 10-15 minutes or take the Silver Line to the World Trade Center

Or - Walk 17 minutes to enjoy an Apres-Ski style menu at Deck 12 where you can eat fondue and drink hot toddies overlooking Boston’s skyline. Heated gondolas and cozy, blanket-laden Adirondack chairs complete the snowy feel.

Price varies | Walk 17 minutes or take the Silver Line to Courthouse Station

Finally - Stroll down Seaport Boulevard to the Rose Kennedy Greenway to see the Hatchlings installation all lit up at nighttime. These sparkling domes, inspired by the Hatch Shell on the esplanade, make a romantic stroll along the Greenway even more magical.

Free | Walk 15 minutes or take the 4 bus to Atlantic Ave at Seaport Blvd

Or - Grab a nightcap at High Street Place food hall where you can pop bottles at the Bubble Bath champagne bar or get creative with craft cocktails at Daiquiris & Daisies. If you’re more of a dessert person, consider a dessert taco from Sugar Skulls.

Price Varies | Walk 12 minutes from Yotel or take the Silver Line to South Station

ODE TO THE OUTDOORS

First - Enjoy a true Boston holiday experience by renting some skates and ice skating on the Boston Common Frog Pond. The city looks magical from the middle of the historic park and as you skate around you can catch a glimpse of the city’s official Christmas Tree all lit up in the Common.

$10+ | Take the Green Line to Park Street

Next - Walk ten minutes through the Boston Public Garden. You’ll want to swing by the Make Way for Ducklings statue on your way through, the ducks are usually decked out in handmade holiday sweaters at this time of year and it’s Instagram gold. Then exit the garden onto Commonwealth Avenue to see the street lit up with festive lights.

Free | Walk ten minutes

Finally - End the evening on a sweet note with a hot chocolate at L.A. Burdick near Copley Square. These rich hot chocolates, available in milk or dark chocolate, warm the body and the soul. If you’re not a chocolate person, try a tea or espresso instead.

Price Varies | Walk five minutes

FRIENDS ARE FOREVER

First - Kick the night off with a stroll through Downtown Crossing searching for the public art pieces that everyone’s talking about. (You know, the big clown heads, among others) See if you can find all of the unique installations in the WINTERACTIVE outdoor exhibition. Bonus points if you do it with a coffee in hand, we recommend George Howell.

Free | Take any Green or Red Line train to Park Street

Next - You’ll probably be a bit chilly after spending all that time outside, so walk over to City Hall Plaza to experience the CultureHouse Finnish-style sauna pop-up. Sweat out those toxins and meet other wellness enthusiasts while you’re at it.

Free | Walk 10 minutes or take any Green Line train to Government Center

Or - Take a tour of Boston’s secret historic library, the Boston Athenaeum, which is home to dozens of beautiful artworks, historic volumes, and cozy reading nooks.

$15 | Walk 10 minutes from Downtown Crossing

Finally - Top off the evening with a glass of bubbly or a craft mocktail at The Wig Shop, a whimsical cocktail bar hidden behind the facade of a former wig shop downtown. If you’re hungry, snack on funky bites like caviar with potato chips and Wagyu sliders.

Varies | Walk 13 minutes or take any Green Line train to Park Street

Or - Enjoy a coffee or tea and a freshly baked Babka at Bakey on Tremont Street. This is no ordinary Babka. Enjoy flavors like Boston Cream Pie, Tiramisu, Chocolate Birthday Cake, and more. You’ll also find fresh bagels and other goodies at this spot.

Varies | Walk 10 minutes from City Hall or the Boston Athenaeum

FAMILY FIRST

First - Attend the weekly Jeff Jam Singalong at Play Union in Union Square. This (free!) singalong starts the day off joyfully and allows you and your child to sing, dance, and meet other like-minded families in the neighborhood.

Free | Take the Green line to Union Square

Next - Walk down the street to Bow Market to grab lunch and explore the shops. With so many different vendors, everyone can have something they love for lunch, even the pickiest of eaters. Bonus points if you can eat around one of the courtyard fire pits.

Varies | Walk 2 minutes

Finally - Head to the super kid-friendly Lincoln Park where your littles can burn out their energy on playground equipment, climbing structures, field space, and walking trails. Older kids can take advantage of the skate park and basketball courts.

Free | Walk 5 minutes

SOLO ADVENTURE

First - Enjoy an ode to the independent at the Isabella Stewart Gardner Museum, a stunning art museum created by a groundbreaking Boston woman who did everything her own way. Pro Tip: Every first Thursday of the month you can get free admission to the museum and enjoy hands-on art-making activities, live music performances, and film screenings.

Free on First Thursdays or $13-20/tickets | Take the E Line to the Museum of Fine Arts

Next - Walk five minutes to Time Out Market to grab a snack at one of the diverse food vendors on site. Representing some of Boston’s coolest restaurants, you can sample sushi tacos, fried chicken sandwiches, bacon-laden donuts, craft cocktails, and much more all under one room. On many nights Time Out has a live DJ, drag shows, or other activities.

Price Varies | Walk five minutes

Or - For a fancier feel, grab a seat at the marble bar of D.W. French and dine on classic Parisian dishes like steak frites, croque madame, and mussels or try more adventurous concoctions like a beef bourguignon sandwich.

Price Varies | Walk 13 minutes from the Gardner Museum

Finally - Cement your royal status by heading to Matcha Cafe Maiko for soft-served matcha ice cream decorated with 23.75K gold. The shop also has shaved ice, hot lattes, teas, and frappes, as well as baked goods to top off the evening.

Price Varies | Walk five minutes

Or - Check out Equal Measure, a new speakeasy-style cocktail bar behind the updated Eastern Standard. Order from the dynamic menu or ask the bartenders to mix you up with special beverages based on the flavors you love.

Price Varies | Walk 7 minutes from Time Out Market or 10 minutes from D.W. French

Photo by @oschapov

How to Spend a Cold Day in Boston

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