Fenway Park, Boston

Best Things to Do in Boston

BY Fifty Grande Editors | August 10, 2020

Welcome to Fifty Grande’s Best of the U.S. Bucket List series. This is your one-stop travel guide to the best, most unique and quintessential experiences of a city, state or event. Want to know how to “do” Boston? We’ve got you covered. Curated by experts, vetted by in-the-know locals, this is all you need to have the best trip ever. If we’ve written a Bucket List, we recommend you go. If it’s on this list, it’s the best the city has to offer right now. Consider this your one-stop answer to “What are the best things to do in Boston?”

When you hear “Boston,” your mind might conjure fifth-grade textbook images of colonists heaving tea into the harbor and ol’ Ben Franklin addressing the Founding Fathers. You’re not wrong. Boston is the birthplace of the Revolution, the so-called “Cradle of Liberty.” If you’re trying to tour historical sites to uncover America’s past, Nicolas Cage style, this is the place to do it. (Side note: Have you ever seen this SNL skit? Hysterical. ) But don’t ignore the city’s more recent 200 years. That’s when Beantown developed into an intellectual and innovation hub, a culinary destination and a thriving art and music town. Here, we’ve painted a picture that’s larger than historical attractions. Here’s a guide to exploring the very best things to do in Boston right now.

You’re here for fresh-caught oysters

Make this a rule: Don’t spend time in New England without enjoying the seafood. Boston’s first-rate oyster bars get their shelled delicacies fresh from the net. 

Row 34, Boston
Row 34, Boston

Row 34

383 Congress St, Boston, Massachusetts, USA

An open, industrial dining area sets the tone for fresh oyster platters and a great selection of local beers. 

B&G Oysters, Boston
B&G Oysters, Boston

B&G Oysters

550 Tremont St, Boston, MA, USA

A South End neighborhood mainstay, they’ve got oysters from both coasts alongside a menu of other seafood classics. You can even take an oyster shucking class. 

You’re also here for drinks

Are you a beer lover or a craft cocktail connoisseur? Like to keep it low-key or get a little weird? Boston runs the gamut. Enjoy standard Boston fare at The Black Rose, or a legendary local cocktail innovation at Drink or The Hawthorne. Prefer your liquor neat? Head to a distillery like Bully Boy or GrandTen. Then, of course, there’s Samuel Adams Brewery and the slew of craft beer visionaries that followed (and did some pioneering of their own).

Black Rose
Black Rose

The Black Rose

160 State St, Boston, Massachusetts, USA

Boston’s classic, authentic Irish pub, serving pints of Guinness, shots of Jameson, shepherd’s pie and other Irish staples. 

Hawthorne, Boston
Hawthorne, Boston

The Hawthorne

500a Commonwealth Avenue, Boston, Massachusetts, USA

A sleek and stylish lounge with creative and locally-renowned cocktails. 

Drink, Boston
Drink, Boston


348 Congress St, Boston, Massachusetts, USA

Another cocktail landmark, one built around community. And there’s no menu. Just tell the bartender what you like and they’ll whip up a personalized beverage. 

Sam Adams, Boston
Sam Adams, Boston

Samuel Adams Brewery

30 Germania St, Boston, Massachusetts, USA

The namesake of America’s original craft brewer has inspired a generation of local craft beer pioneers like Harpoon Brewery, Cambridge Brewing Co. and Dorchester Brewing.

Spark your creativity

At first glance, Boston might seem like a sports town, then a food town, then a tech town. But don’t forget that it’s also an arts town. And nowhere is that art scene thriving more than SoWa.

Sowa, Boston
Sowa, Boston

SoWa Art + Design District

450 Harrison Ave, Boston, MA, USA

SoWa (South of Washington) is the right brain to MIT’s left brain — it’s artistic and expressive, a thriving nerve center of creativity. Hop between contemporary art galleries, design showrooms, boutiques, restaurants and food markets. If you’re in town on a Sunday, don’t miss the SoWa Open Market, a regionally acclaimed gathering of farmers, chefs, artists, musicians and more. 

What to do for an afternoon

Get out and see what only Boston offers. 

Harvard University in the spring
Harvard University in the spring

Harvard University

Harvard University, Cambridge, MA, USA

One of the nation’s most prestigious institutions, Harvard is perfect for sightseeing too. Spend an afternoon wandering the campus admiring some of its Victorian architecture. In Harvard Square you’ll find shopping, eating, drinking, live theater, movies and more. 

Boston Common
Boston Common

Boston Common

139 Tremont St, Boston, Massachusetts, USA

If you get tired of busy city streets and crowded restaurants, you might need a dose of green space. Boston Common, located in downtown Boston, was established in 1634, making it the oldest American city park. Today, it’s a tranquil escape from city life, complete with walkways, baseball diamonds and a frog pond. You might even find yourself at a wedding.

Fenway Park in Boston
Fenway Park in Boston

Fenway Park

Fenway Park, Jersey Street, Boston, MA, USA

Google “historic baseball parks.” If Fenway Park isn’t one of the top results, check your search for typos. Boston Red Sox fans have been listening to the crack of the bat here since 1912, making it America’s oldest active ballpark. You might even get a seat atop the “Green Monster,” Fenway’s exceedingly tall left-field wall and popular home run target. 

Mapparium, Boston
Mapparium, Boston


200 Massachusetts Avenue, Boston, MA, USA

Africa is nearly 15 times larger than Greenland, but you’d never know it by looking at a flat world map. The Mapparium, a three-story-tall, stained-glass globe, accurately portrays the relative sizes and locations of countries and continents. And you walk through the map, so you step right into a 360-degree view of Earth and literally see the world from a new perspective.

Bowl Haven, Boston
Bowl Haven, Boston

Candlepin Bowling at Sacco’s Bowl Haven

45 Day St, Somerville, Massachusetts, USA

Ask about candlepin bowling outside of New England and you’ll only get confused looks. That’s because no one else plays it. But ask New Englanders and some will argue that tenpin bowling can’t hold a flame to candlepin (pun absolutely intended). It’s played with a grapefruit-sized ball and tall, thin pins that resemble — you guessed it — candles. 

Get revolutionary

The Boston Tea Party, the Boston Massacre, the Battle of Bunker Hill — we could go on and on. Boston is loaded with American Revolution history. 

Freedom Trail starting point
Freedom Trail starting point

Freedom Trail

Freedom Trail Starting Point, Freedom Trail, Boston, MA, USA

This “American history crash course” walking tour is 2.5 miles long and takes you through the heart of downtown Boston, passing 16 revolutionary icons, including the Paul Revere House, USS Constitution, Massachusetts State House, Old South Meeting House, Bunker Hill Monument and Old North Church (of “one if by land, two if by sea” fame). You have the option to take a guided tour or plot out your own trail.

Sample the city’s best lobster rolls

Massachusetts fishermen haul in millions of lobsters each year. Where do they go? Most often, in between two buns with mayo, lemon and seasoning. Despite what some purists might tell you, Maine doesn’t have a monopoly on good lobster rolls. The Boston area has its fair share too. Too many to try on one trip, unless you’re pounding lobster for breakfast, lunch and dinner — which, actually, isn’t a bad idea.

Pauli's, Boston
Pauli's, Boston


65 Salem St, Boston, Massachusetts, USA

An affordable North End sub shop with seafood and Italian menu options. They call their lobster roll a “symphony of shellfish,” and it’s hard to argue.

Yankee Lobster Co., Boston
Yankee Lobster Co., Boston

Yankee Lobster Co.

300 Northern Ave, Boston, MA, USA

Owned by a long-time fishing family, they’ve got all kinds of Boston seafood classics and local beers. 

James Hook, Boston
James Hook, Boston

James Hook & Co.

440 Atlantic Ave, Boston, Massachusetts, USA

It might look like a waterfront fishing shack, but this family business is still serving up incredibly fresh whole cooked lobsters (and showstopper lobster rolls) after several decades.

See a show at a storied local venue

If your favorite artist is going on tour, they’re probably stopping in Boston along the way. This town has venues for every interest and vibe.

Paradise, Boston
Paradise, Boston

Paradise Rock Club

967 Commonwealth Avenue, Boston, MA, USA

Located right on Commonwealth Ave., at the edge of Boston University’s campus is the Paradise.  It’s intimate, 933-person room has hosted shows since 1977. Alt-rock legends like R.E.M. and Phish, hip-hop stars like Denzel Curry and Playboi Carti and many more have played here. 

Middle East, Cambridge
Middle East, Cambridge

The Middle East

472-480 Massachusetts Ave, Cambridge, Massachusetts, USA

A Cambridge mainstay that’s hosted live music since the 1975, the Middle East is a local icon for rock, indie rock and hip hop shows. It’s a former Lebanese restaurant that’s expanded into five adjacent dining and live music venues, which makes the vibe unique and completely its own. 

Visit a world-class museum

Boston has a wealth of museums, so many that, unless you’re a museum junkie, you’ll have to pick and choose. If you’re into art, try the Museum of Fine Arts, the Institute of Contemporary Art or the Isabella Stewart Gardner Museum. Or, if the Freedom Trail didn’t quite satisfy your history craving, go for the USS Constitution Museum, the Boston Tea Party Ships & Museum or the Harvard Natural History Museum. Nature lovers prefer the New England Aquarium or Arnold Arboretum instead. Or for a more niche experience, head to the Museum of Bad Art or the Warren Anatomical Museum.


Go on a cannoli crawl in North End

Don’t skip dessert when you head to “Boston’s Little Italy.” The North End boasts some tantalizing bolognese and focaccia, but the real test for Italian eateries here is that post-dinner, ricotta-filled pastry: the cannoli. The big decision, though, is where to get one. Local favorites include Mike’s Pastry, Bova’s Bakery, Maria’s Pastry Shop and Modern Pastry. 

Mike's Pastry
Mike's Pastry

North End neighborhood

North End, Boston, MA, USA