trillium beer garden boston
Courtesy
Courtesy

The 20 best things to do in Boston

Experience the absolute best of the city this winter with our epic guide to essential eats, drinks, culture, and more.

Cheryl Fenton
Advertising

Winter is in full swing in Boston. Parks and city trails have quieted down with activity, and restaurants and bars are filled with patrons who want to escape the chilly temps while enjoying what the city's dining scene has to offer. Museums and other indoor attractions are also welcoming an influx of visitors who want to enjoy what the city offers from the comfort of heated confines.

Below, find your ultimate guide to the best things to do in Boston this winter for tourists and locals alike. The ordering is intentional. The top items are the most essential things to do on a first trip to Boston. Returning visitors and those with a lengthier itinerary can explore further down the list to find worthwhile attractions, museums, and fun experiential activities.

Time Out Market Boston

Time Out is a global authority on where to eat right now, and we hand-pick restaurants to represent our cities at Time Out Market. The Fenway food hall and cultural market has more than a dozen dining options plus two bars showcasing local craft beer and seasonal cocktailsBut just like on our website, showcasing the best of the city under one roof goes beyond food and drink. Time Out Market Boston also hosts frequent events like pop-up markets, free fitness, drag brunch and more. Here's an updated list about what's going on this month.

Best things to do in Boston

What is it? One of the coolest streets in the world, Boston’s version of Fifth Avenue is perfect for both shopping, dining and people-watching.

Why go? Between Arlington Street and Massachusetts Avenue, there are eight blocks of beautiful brick townhouses housing anything from ultra-luxe designers and chic boutiques to affordable international chains. With a never-ending assortment of galleries, salons, cafés, bars and eateries to explore, you can easily spend an entire afternoon browsing, relaxing and indulging here.

Don’t miss: Fans of architecure and home decor shouldn't miss a stroll through the four floors of Restoration Hardware, which is housed in the gorgeous former home of the Museum of Natural History. 

Need some guidance? Book a tour that includes Newbury Street. 

  • Museums
  • Art and design
  • Mission Hill

What is it? Modeled on a Venetian palace and mostly untouched from the eccentric collector's time in Boston, the former home of American art collector Isabella Stewart Gardner is a sightseeing gem.

Why go? The museum's most famous treasures remain exactly where Gardner had arranged them, including the empty frames that once held priceless works of art stolen during the infamous 1990 theft (watch this documentary on Netflix for more information about that). The museum also boasts a flower-filled courtyard that blooms all year long. 

Don’t miss: A late-night visit to the museum on Thursdays, when the museum is open till 9pm and welcomes live performances in the stunning courtyard while you breeze through the galleries. It's free on the first Thursday of the month. 

Advertising
  • Attractions
  • Towers and viewpoints
  • Back Bay

What is it? You've done a little exploring of Boston on the ground, now see what it looks like from high above at View Boston, a stunning observatory that takes up the top three floors of the iconic Prudential Tower. (That's 52 stories up!) 

Why go? The immersive attraction offers visitors a personalized perspective on the city, with interactive displays featuring tidbits about Boston art, music, history, neighborhoods and more.

Don't miss: Head out to the Observation Deck to see 360-degree views, then grab a drink at Stratus, Boston’s highest rooftop bar. 

4. Spend a day in Cambridge

What is it: With some essential Boston experiences under your belt, consider hoping across the Charles to spend a day in Cambridge, where an excellent day of shopping and Ivy League campus-peeping await. 

Why go: Cambridge is made up of a collection of squares, all of which offer an excellent selection of thrifts shops, home goods stores, ice cream shops, restaurants, dispensaries, bars and more. The uninitiated can get a perfect overview walking along Massachusetts Avenue between Central and Harvard squares, where the vibe is more Haight-Ashbury than Ivy League. 

Don't miss: Dinner! Cambridge is home to some of the very best restaurants in Boston. Try Judy's Bay, a hip haunt for Japanese. Puritan & Co. offers an updated spin on traditional New England fare. Urban Hearth sets a standard for farm-to-table restaurants everywhere.  

Advertising

What is it? You can't visit Cambridge without at least stepping a toe on the grounds of the oldest university in the States. 

Why go? These iconic red brick walls contain some truly remarkable stories, and a visit will connect you to a Whos Who of American history. Just imagine all the people who studied here — from John Adams to Barack Obama and Natalie Portman to Bill Gates. The Yard and overall campus features striking architecture designed by such luminaries as Bulfinch, Le Corbusier (his only American building) and Sert.

Don’t miss: Harvards Museum of Natural History is a fun visit. It houses some cool dioramas, an enourmous gem collection and a groundbreaking and absolutely awe-inspiring collection of glass flowers and plants. 

  • Attractions
  • Libraries, archives and foundations
  • Back Bay

What is it? The Boston Public Library (BPL) contains approximately 19 million volumes and electronic resources, making it the second-largest public library in the U.S.—coming right behind the Library of Congress.

Why go? At nearly 1 million square feet, the main branch in Copley Square impresses in a way that few libraries can. The original structure, designed by Charles McKim and completed in 1895, now serves as the research library, while an extension (opened in 1972) functions as the general library. Talks, performances and tours delight culture vultures from near and far.

Don’t miss: At the center of the library is a cloistered courtyard, one of the citys most beautiful, tranquil places to read a book.

Want to see more in the area? Book a tour

Advertising
  • Museums
  • Art and design
  • Seaport District

What is it? The dramatic, glass-walled ICA is the cultural cornerstone of the buzzing Seaport District. 

Why go? The 65,000-square-foot building houses galleries, a theater and a café. The museum staff prides itself on providing a platform for challengingsometimes controversialworks. After youve contemplated the art, retreat to the scenic outdoor deck, the site of live performances and events. Note: Admission is free on Thursdays from 5pm-9pm.  

Don’t miss: The latest special exhibition at ICA offers a colorful world-debut retrospective of abstract painter and printmaker Stanley Whitney. Catch it on view through August. 

Save money on tickets with a Go Boston Pass

  • Attractions
  • Libraries, archives and foundations
  • Fenway/Kenmore

What is it? Located inside the Mary Baker Eddy Library, the Mapparium is essentially a three-story model of the globe built to scale. 

Why go? This colorful sphere runs 30 feet in diameter and can be crossed by means of a glass bridge bisecting its interior. Inside, sound bounces off the rooms rounded walls, amplifying it tenfold, so keep in mind that there are no secrets in the sphere—no matter how softly you may whisper.

Don’t miss: The 608 stained-glass panels recreate the world as it was in the mid-1930s, when the project was completed. So keep keen eyes on those outdated borders.

Save money on tickets with a Go Boston Pass

Advertising
  • Things to do

What is it? If you've been in Boston for any length of time, you've probably checked out the Museum of Science, the MFA, the Institute of Contemporary Art and maybe even the Isabella Stewart Gardner Museum. But there are more under-the-radar museums that will add to your understanding of the city, from the West End Museum, paying homage to one of Boston’s almost forgotten neighborhoods; to the Museum of Bad Art (co-located with Dorchester Brewing Company!).

Why go? These niche museums present art and artifacts, mostly with a hyper-local focus. 

Don't miss: The Gibson House Museum in Back Bay is a 1859 rowhouse, and a time capsule of what life was like in Boston from the mid-19th to early-20th centuries.

  • Attractions
  • Zoo and aquariums
  • Waterfront
  • Recommended

What is it? New England’s largest aquarium and one of Boston’s most popular attractions.

Why go? More than 80 African, rockhopper and little blue penguins live in the New England Aquarium’s first-floor display. Watch them go wild during feeding time in front of the Giant Ocean Tank, a massive coral reef exhibit that's home to a myriad of other marine creatures, including sharks and loggerhead sea turtles. The building is designed in such a way that the penguins can be seen from multiple vantage points. 

Don’t miss: Be sure to say hi to the harbor seals in their enclosure outside, which is free and open to the public.

Advertising
  • Attractions
  • Zoo and aquariums
  • Roxbury
  • Recommended

What is it? The citys quaint zoo is a kid-friendly local favorite.

Why go? As fascinating as animals seem on the TV screen, they’re far more impressive in real life. The zoo—whose mission is to inspire people to protect and sustain endangered species—is home to zebras, gorillas, giraffes and a host of other exotic animals that you definitely wouldn’t normally see in the wilds of New England. 

Don’t miss: Franklin Park Zoo recently welcomed a handsome 6-year-old clouded leopard named Jye. Stop by to say hello in the Tropical Forest Pavilion. 

  • Pizza
  • Somerville

What is it? Candlepin bowling is uniquely New England—the pins are tall and much thinner than those of standard 10-pin, and balls are closer to softball-sized. A local favorite for playing this regional game is the lovingly maintained Sacco’s Bowl Haven, which dates back to 1939 and now sits inside a pizza restaurant in Somerville. For something lower-key, there's also Ron's Ice Cream and Bowling in Hyde Park. 

Why go? The accompanying grub! Sacco's sells amazing thin-crust pizza and a great selection of local craft beer. The ice cream at Ron's is so good, it's worth a trip on it own. 

Don’t miss: It's always smart to reserve a lane before you visit either of these spots. 

Advertising
  • Cocktail bars

What is it? Given the area’s renowned reputation for the sciences, its no surprise that Boston has a bevy of talented mixologists.

Why go? Why go out for a simple beer when you can order an immersive sensory experience in a glass? For a truly mind-blowing cocktail, head to local trailblazers like Farmacia and Equal Measure (which was just named a best bar in North America), both of which offer an expansive list of truly unexpected sips.

Don’t miss: For a next-level experience, try cocktails featuring house-made tinctures and shrubs at Parla. The North End spot even offers a dice game that lets you gradually unlock a secret drink menu.

What is it? For a city that’s often limited by its strict, booze-related blue laws, we sure have a fine collection of breweries. 

Why go? Historically, Boston's most recognizable brewer was Samuel Adams, the revolutionary and “maltster” for whom the city's biggest beer brand is clearly named. Suds-loving tourists should certainly visit the Samuel Adams Brewery in Jamacia Plain, but an exploration of Boston's booming craft brew scene should also take priority. Join locals in tasting small-batch, farmhouse-style ales at Fort Point’s Trillium Brewing Company; experimental suds at Somerville’s Aeronaut Brewing Company, founded by a science-focused trio with MIT connections; and inventive brews at Roundhead Brewing Company in Hyde Park, which also makes some of the best pizza around. 

Don’t miss: Any of the lively, beer-fueled festivities at the Harpoon Brewery.

Advertising

What is it? Boston is famous for its fresh seafood, so enjoying a dozen local oysters at one of the city’s top raw bars is a must.

Why go? Ever since the Union Oyster House opened in 1826, raw oysters have been integral to Boston’s culinary scene. Today, these briny bivalves appear on restaurant menus throughout the city. You'll find locally sourced varieties including Wellfleet, Cotuit and Glidden Point as well as popular imports like Kumamotos. Oyster happy hours are a great way to sample these goodies at a lower price.

Don’t miss: Island Creek Oysters' farm is a destination-worthy day trip in Duxbury, about an hour south of Boston. The outdoor raw bar boasts views of the harbor where these delicious delicacies grow and thrive. 

  • Pubs

What is it? Boston’s collection of cozy, welcoming Irish pubs like The Burren and The Druid all but guarantee a lively night of craic

Why go? In a city chock full of proud Irish expats and Irish-Americans, it’s little wonder why Boston is brimming with an excess of quality pubs. To get the full experience, head in on a spirited trivia night, or during a live performance of authentic Irish music.

Don’t miss: For a centrally located option with nightly live tunes, look no further than the Black Rose.

Advertising
  • Clubs

What is it? There are many opportunities to laugh your socks off this season at one of Boston's veteran comedy clubs and other venues. The Improv Asylum in the North End has a loyal following, especially when it comes to the more risque late-night shows.

Why go? Some of America’s most popular contemporary comedians like Conan O’Brien and Bill Burr honed their craft in Greater Boston.

Don't miss: Think you have what it takes to crack some jokes for a crowd? Consider one of the improv classes at Improv Asylum this spring. 

  • Food court

What is it? The food hall trend is strong in Boston, with a wealth of them thriving around the city.

Why go? Offering numerous cuisines and drink options all in one spot, food halls are a great choice when you’re dining with a group—there’s something for everyone. They make for a great anytime meeting spot; just show up and see what kind of mood you’re in.

Don't Miss: Eataly is a haven for Italian food enthusiasts. The Boston Public Market is a quaint visit with fresh produce, cheeses, prepared foods and even home goods. And Time Out Market Boston showcases the best of the city under one roof. 

Advertising
  • Museums
  • History
  • Dorchester
  • price 2 of 4

What is it? Located behind UMass Boston’s Dorchester campus, the JFK Presidential Library and Museum occupies a dramatic concrete-and-glass monolith by architect I.M. Pei.

Why go? The captivating multimedia exploration of the former president's life remains a draw, alongside engaging temporary exhibits and special events delving into politics, culture, and current affairs. Ascend to the ground floor, where the breathtaking atrium offers sweeping vistas of the sea and cityscape. Below, the museum unfolds with a rich collection of memorabilia and a dynamic rotation of temporary exhibitions. 

Don’t miss: A special exhibition this summer will spotlight presidential pets throughout the history — from Herbert Hoover's King Tut to Bill Clinton's cat Socks. 

  • Things to do
  • Everett
  • Recommended

What is it? A little slice of Las Vegas in New England, Encore Boston Harbor is a mega-casino resort just outside the city in Everett.

Why go? The 210,000-square-foot complex—which cost nearly $3 billion to build—includes 15 high-end dining and lounge venues, an ultra-premium spa and more than 600 guests rooms for the ultimate staycation. 

Don't miss: The four-season, six-acre Harborwalk features pedestrian and bike paths, a picnic park, a gazebo, viewing decks, waterfront dining and lush green space with magnificent floral displays.

Best restaurants in Boston by cuisine

Advertising
Advertising

Need somewhere to stay?

Advertising

More great things to do across the globe

Recommended
    More on city identity
      You may also like
      You may also like
      Advertising