A cultural guide to Boston

Boston is a place where coastal beauty comes with a hint of New England saltiness. The city made it known, in December 1773, that it wouldn’t take guff from anyone—certainly not Britain and its taxation without representation, so citizens tossed 342 crates of tea into the harbor, launching the colonies’ fight for independence.  

That tea-tossing determination lends itself to the city’s small-but-mighty persona, dense with top universities, art, innovation, culture, and its storied sports culture. From the Red Sox’s legacy of grit and glory to Bostonians’ can-do attitude, the city’s universal appeal is hidden in plain sight. 

Art & architecture

Art is ever-present in Boston—from time-honored institutions like the Museum of Fine Arts Boston to Dorchester Brewing Company’s beloved Museum of Bad Art. Then there’s the enchanting grounds of Fenway’s Isabella Stewart Gardner Museum, the site of the world’s largest—still unsolved—art heist. See works by the likes of John Singer Sargent, which compete for visitors’ attention when the kaleidoscope of blossoms make their annual debut in the open-air courtyard. 

Be sure to add the 1806 African Meeting House to your architecture checklist (find it on the Black Heritage Trail), as well as key stops on Boston’s Freedom Trail, including the Georgian King’s Chapel (1754) and the Old North Church of Paul Revere fame. Additionally, visit the breathtaking Central Library at Boston Public Library, and the city’s oldest public building, the Old State House.

And don’t miss the North End’s Spite House, an architectural manifestation of sibling squabbles, Boston-style. The legend goes that when two Civil War-era brothers inherited the land, one built a house on it without the other knowing—in retaliation, the second brother built a very skinny, very inconvenient house on the rest of the land to block entry.  

Shopping

Back Bay’s Newbury Street deserves its spotlight, offering luxury storefronts like Chanel, but a few blocks west of the Public Garden, many shops are edgier and locally owned. Other iconic shopping spots include Faneuil Hall Marketplace, built in 1742. Though the vendors have changed, the vibrant hum remains as pushcart vendors chat up visitors and fishmongers tout their daily catch. 

Then there’s SoWa Boston—the soulful art and design haven in the South End. Lose a few hours here digging through new and reclaimed art, high-end craftsmanship, boutiques, and vintage markets. Or dabble in Boston’s thriving bookstore scene, anchored by historic Brattle Book Shop (think antiquarian tomes and alleyway sale racks). Independent and pop-up bookstores seem to sprout up weekly, like the inclusive romance bookshop Read My Lips or the cozy Beacon Hill Books & Café. 

Sports

For some, traveling to Boston is a pilgrimage to the oldest ballpark in Major League Baseball. When Fenway Park opened in 1912, then-owner John I. Taylor put up a high-for-the-time fence to prevent anyone from watching games for free. Over the years, the wall—dubbed the Green Monster—grew in fame, and in 2003 seats were introduced allowing fans to watch the game from its peak. Below, the park’s still-in-use hand-operated scoreboard offers a wink to days of yore.  

What’s more, there’s a large window where The Bleacher Bar patrons can watch warm-ups without a game ticket. Take a tour of Fenway Park and even get a glimpse of Fenway Farms, the park’s rooftop garden, which produces up to 6,000 pounds of fragrant herbs and produce per year.  

Meanwhile, sports enthusiasts can catch a Celtics or Bruins game at TD Garden or get in on the action by visiting the Seaport’s funky electronic dart haven, Flight Club, or ping-pong bar, SPIN. 

Watch before you go

Childhood friends turned actor-producers Matt Damon and Ben Affleck made their names in the film industry in 1997 when they premiered Good Will Hunting—set in their hometown, Boston. Their characters’ favorite bar, Southie’s L Street Tavern, still welcomes locals and visitors alike. Find the Boston Public Garden bench where Robin Williams delivered his Oscar-winning monologue to Damon. Meanwhile, The Departed and Spotlight are standouts, together with long-running series Cheers, which ended in 1993 but still draws fans to the Beacon Hill bar that inspired it.