Things to do in Boston

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Discover the Best Activities in Boston

In the 17th and 18th centuries—America’s formative years—the Boston played a starring role in the country’s fight for independence. In the 19th century, some of America’s most influential doers and thinkers called Boston home, justifiably dubbing it the “Hub of the Universe.” In the 20th century, Beantown experienced—writ large—the same growing pains sweeping the rest of the nation, including immigration booms, civil-rights battles, and problems with urban expansion and renewal. On this side of the millennium, Boston at times seems to trump up its illustrious past too aggressively. It’s true that the well-trampled Freedom Trail does revisit some of the most important moments in US history, but this most American of American cities didn’t earn the title of “America’s Walking City” for one measly 2.5 mi. stroll. Boston is a restless stew of compact neighborhoods, dramatically distinct communities, winning cultural attractions, and acres of urban parks—all of which are best sampled on foot. While the Freedom Trail is a nice place to start, wandering around Boston’s many different districts, its jumble of streets, and it’s (rarely square) squares will give you a glimpse of a still-evolving metropolis where tired history is less important (and less fascinating) than the lives of those who live in the city today.

Top Things to Do in Boston

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Get to Know Boston

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Get Oriented

Boston’s heart is the grassy Boston Common, sandwiched between Beacon Hill to the north, downtown to the south and east, and Back Bay to the west. Back Bay is Boston’s most navigable area. Major avenues Beacon Street, Commonwealth Avenue, Newbury Street, and Boylston Street run parallel to Storrow Dr.; alternating one-way cross streets are named alphabetically from Arlington to Hereford as you head west. Elsewhere, driving is more complicated. The Big Dig that once wreaked havoc on the roads of the waterfront now eases the flow of traffic at the intersection of I-93 and I-90 (Mass Pike), which divides the city going east-west. The labyrinthine cobblestone paths of Boston’s colonial downtown and the North End are difficult to navigate and will leave you wishing for flaxen thread or wax wings.

See & Do

What to do in Boston

Ahhh, can’t you just smell the history? Boston tells many a tale with its historical sights, but it’s also a modern city with dozens of beautiful parks and exemplary museums. Boston is so compact and walkable that you can see and do most everything you want on foot—there’s a reason they call it America’s Walking City. For the most famous walk of all, head to the Freedom Trail in the heart of the city. For those of you interested in outdoor activities, there are many places for swimming, canoeing, hiking, etc., that are accessible by a short drive, but these aren’t nearly as legitimate as the outdoor activities that can be reached on daytrip from the city. Though the brick sidewalks of Harvard Sq. may seem far from the trails of the White Mountains, the scenic journey to the rest of New England passes quickly and painlessly.

Top Attractions in Boston

Short on time, but don’t want to miss out on Boston’s best? Check out our top picks. Click the links to explore and book tours or local guides.

Eat & Drink

Whether your car is loaded down with twin teenage daughters looking at colleges or a pack of recent Stanford grads jealously hobnobbing at Harvard, Boston’s dining establishments are a gastronomic playground for all passengers. Trendy bistros, fusion restaurants, and a globetrotting array of ethnic eateries have taken their place alongside the longstanding “chowda” shacks, greasy-spoons, soul-food joints, and welcoming pubs. The city prohibits the use of trans fats in all dining establishments, and organic and local options are common.


Though Downtown does not offer the most unique eating in Boston, its history and locale are difficult to beat. Sandwich shops pop up on almost every corner and the diverse food court inside Quincy Market are affordable. Fresh seafood shops line Boston’s Waterfront district.

North End

Boston’s Italian-American enclave is the place to go for authentic Italian fare, with over 100 restaurants packed into 1 sq. mi. With narrow streets and dim lighting, it is the perfect spot for a cutsie date or girls night out. Most establishments line Hanover St., accessible from Haymarket. After dinner, try the cannoli and other Italian sweets at Mike’s Pastry or Modern Pastry.


Boston’s Chinatown doesn’t throw any curveballs. A destination for cheap, filling Asian food at nearly anytime of the day, Chinatown is the closest you can get to Beijing or Hong Kong in New England. Stuck between the skyscrapers of the Financial District and the Theater District, the neighborhood is slightly grimy and run-down, but the prices are unbeatable and most places stay open late.

Back Bay

The diverse eateries of the Back Bay line elegant Newbury St., accessible from The Hynes Convention Center or Back Bay. Though Newbury is known as Boston’s most expensive shopping district, affordable restaurants do exist here.

South End

The long waits and hefty bills at these establishments are worth the expense. The South End’s upscale restaurants meld flavors and techniques from around the world with amazing results. Most eateries line Tremont St., accessible from Back Bay.

Arts & Culture

Boston in Print

Boston has long held the printed word in high regard—a tradition begun by Bible-reading Puritans and continued today in its many colleges.

Many famous American authors called the Boston area home. In the mid-19th century, the heart of the Transcendental movement was in Concord, and the most important American writers would gather at their publishers’ home, the Old Corner Bookstore, at Washington and School St.


  • Anne Bradstreet (1612-72). As a Puritan woman, she wrote poetry about the trials of the New World. Her work describes the beauty of the New England landscape as well as tragedies, like the death of her children, that occurred in the young colony.
  • Phillis Wheatley (1753-84). A colonial-era slave who began writing at the age of 12 at the encouragement of her master, she is recognized as a major female poet in American letters, though few of her works survive.
  • Henry Wadsworth Longfellow (1807-82). A longtime Cantabrigian, he immortalized largely mythologized accounts of great American events in verse, including “Paul Revere’s Ride.” His Cambridge abode was a popular literary gathering place.
  • Robert Lowell (1917-77). Descended from pure Boston Brahmin stock, Lowell wrote countless poems about life in Boston, the most famous (and cryptic) of which is “For the Union Dead,” an eerie depiction of the city in winter. Lowell spent much of his life in and out of McLean, a psychiatric hospital in Belmont, just west of Cambridge.


  • Ralph Waldo Emerson (1803-82). The father of Transcendentalism, Emerson has influenced writers from the 19th century to the present. Most of his works are essays on the relationship between man and society and make excellent light reading.
  • Nathaniel Hawthorne (1804-64). Though best known for his Puritan-era novel The Scarlet Letter, Hawthorne also contributed a wealth of novels and short stories to the American literary vault while living in Salem and the Old Manse in Concord.
  • Henry David Thoreau (1817-62). Thoreau followed Emerson both to Concord and to the philosophy of Transcendentalism. After refusing to pay taxes due to opposition to the Mexican War, Thoreau spent a night in jail and wrote “Civil Disobedience.” His most famous work is Walden, in which he recorded his time living in solitude along the shores of Walden Pond—though the romance might fade when you learn that Thoreau walked into Concord center several times a week to dine and visit with friends.
  • Louisa May Alcott (1832-88). Her novel Little Women was based on her own experiences growing up with 3 sisters. Alcott wrote the famous sisterly epic from the Orchard House in Concord, where she and her family lived.

Books About Boston

  • The Scarlet Letter (1850). Puritan woman commits a steamy act of adultery—but most of the book is about her relationship with society after that happens.
  • The Bostonians (1886). Bostonian Henry James pits traditional Brahmin values against “radical” feminist suffrage in a detail-riddled period novel about a supposedly pseudo-lesbian love affair. Particularly tragic satire.
  • T Make Way for Ducklings (1941). Robert McCloskey’s children’s classic follows Mr. and Mrs. Mallard as they lead their 8 ducklings past countless Boston landmarks en route to the Public Garden, where real-life statues commemorate their fictional visit.
  • Johnny Tremain (1943). Esther Forbes’s Newbury Award-winning book about a young silversmith’s apprentice suddenly thrown into the thick of the Revolution is an excellent introduction to the historical events that shaped both Boston and the nation.
  • The Crucible (1953). Arthur Miller’s play based on the Salem Witch Trials was actually written in response to the McCarthy communist witchhunts of the 1950s.
  • The Handmaid’s Tale (1985). Margaret Atwood writes about a dystopia a la 1984, except much more feminist. As you follow the title character around her far-right totalitarian state, it will suddenly dawn on you in horror… She’s writing about Cambridge!
  • Asa, As I Knew Him (1987). Cambridge author Susanna Kaysen’s witty novel perfectly depicts the bookish climate of her town (complete with an intellectual love affair), then suddenly flashes back in time to examine the privileged life of those living on Cambridge’s old Tory Row. Kaysen based her better-known Girl, Interrupted on her time at McLean Hospital in nearby Belmont.
  • A Drink Before the War (1994). The 1st of Dennis Lehane’s “Kenzie and Gennaro” detective novels follows the 2 Dorchester-based sleuths as they attempt to uncover corruption and racism in Boston’s government. From Beacon Hill to Savin Hill, this often gruesome, always hard-boiled thriller paints a horrifying portrait of racial, political, and socioeconomic tensions in and around Boston.
  • The Dante Club (2003). Henry Wadsworth Longfellow, Oliver Wendell Holmes, and James Russell Lowell solve murder mysteries while translating The Inferno; no wonder Matthew Pearl’s historical fiction debut became a fixture on national bestseller lists.
  • In addition to the works below, local historian Anthony Mitchell Sammarco has written over 25 “neighborhood biographies” (e.g., Boston’s North End, Roxbury, and Jamaica Plain), each using vivid prose, period photos, and countless artifacts to trace the history of a different district in the Boston area.
  • Common Ground (1986). Historian J. Anthony Lukas won a Pulitzer for this intelligent, troubling chronicle of the racially polarizing forced busing crisis, recorded here through 3 different area families (2 white, 1 black) caught up in the turmoil.
  • The Big Dig: Reshaping an American City (2001). Peter Vanderwarker uses photographs, blueprints, interviews, and more to lead younger readers through Boston’s confounding Central Artery/Tunnel Project—not yet finished when he published.
  • Red Sox Century (2005). By Glenn Stout and Richard A. Johnson, this is arguably the best of the many Sox histories out there. Originally published in 2000, it has since been updated to include the rather important events of the 2004 season.

Boston in film

Most movies about Boston are shot outside the city. There are, however, a few films worth seeing that really capture the Greater Boston area.

  • Love Story (1970). Harvard PhD candidate Erich Segal based this passionate, if slightly sappy, tale of doomed romance and class struggle on his late 60s stint as a proctor in the Harvard dorm where actor Tommy Lee Jones and Vice President Al Gore were roommates (they are both supposedly the inspiration for the jock-with-a-heart-of-gold lead of the film). The movie’s bitter weather and tragic, volatile, only-in-the-Ivy-League romance are both terribly painful—and painfully terrible—depictions of life in Boston and Cambridge. For more Harvard lovefests, see also The Paper Chase and Legally Blonde.
  • Good Will Hunting (1997). Written by and starring Boston natives Ben Affleck and Matt Damon, this is the story of a brilliant MIT janitor who woos a comely Harvard student all over Boston while receiving counseling from Bunker Hill Community College professor Robin Williams. Filled with scenes at many area sights; reenact away!
  • Mystic River (2003). Clint Eastwood directs this Oscar-winner about 3 boyhood friends who find themselves on opposite ends of a murder investigation. Not much of an upper, but it does expose much of Boston’s untouristed underbelly. Don’t reenact this one.
  • Fever Pitch (2005). A romantic comedy by the Farrelly brothers that is the best single depiction of Boston’s love for its Red Sox. Many past and present Sox players star.
  • The Departed (2006). A Martin Scorsese joint and winner of Best Picture. Stars from Jack Nicholson to Leo DiCaprio act out the cat-and-mouse game between the South Boston mob and the police. Better accents than in Mystic River.


Boston’s tiny two-block Theater District, near T: Boyston, west of Chinatown, was once the nation’s premier pre-Broadway tryout area. Today it’s a stop for touring Broadway and West End productions, not to mention a lively nightlife district.


Modeled on the world’s most acoustically performed music hall (the Gewandhaus in Leipzig, Germany), Symphony Hall is home to both the Boston Symphony Orchestra (BSO) and its light-hearted sister the Boston Pops. Every 4th of July, the Pops give a free evening convert at the Esplanade’s Hatch Shell, near T:Charles/MGH, with patriotic music, fireworks, and Tchaikovsky’s 1812 Overture – with real cannons.


While the sights along the Freedom Trail testify to Boston’s Revolutionary roots, the city’s true heart beats at the storied Fenway Park. The nation’s oldest, smallest, and most expensive baseball park, Fenway is also home to the Green Monster. At the Gillette Stadium in Foxborough, the New England Patriots grind it out on the gridiron from September to January.

Raced every Patriot’s Day, the Boston Marathon, the nation’s oldest foot race and one of Boston’s greatest sporting traditions, is a 26.2mi. run that starts in Hopkinton, MA, in the west, passes over “Heartbreak Hill,” and ends amid much hoopla at Copley Square. For over 100 years, the marathon has attracted runners from all over the world, and fans flank every inch of the course.

The Head of the Charles Regatta, the world’s largest crew regatta, has drawn throngs of preppies to the banks of the river every October since 1965.


Boston used to be run by Puritans, and it still feels like that at times. Bureaucratic hurdles close down most nightspots by 2am, contributing to the city’s reputation of being a rather mediocre place to party. Clubs are indeed scarce in Boston, but the city is actually a great place for a low-key night out. Its Irish heritage has encouraged an explosion of late-night pubs, and there are certainly plenty of bars of varying swankiness. Where they exist (mainly the Theater District), nightclubs often vary by night; different clubs also have different theme nights, clienteles, vibes, etc. Finally, be aware that Boston is not a city known for its lax carding—that $30 New Jersey ID isn’t getting you anywhere fast.

Get Your Culture On

Newbury St., for most of us, means expensive stores and expensive restaurants, but the beauty of the Back Bay isn’t the well-heeled fashionistas—though their dulce de leche martinis and foie gras hamburgers are oh so tasty—but rather its free art galleries.

Although they may look like museums, galleries don’t charge admission because they’re technically places of business where everything on display is for sale. (They don’t expect you to buy, though, since their sales come pretty much exclusively from established collectors who set up private appointments.) Housed above and amid the Newbury St. shopping scene, they also provide a quiet respite from the designer brands and bags crowding the sidewalk. Many art galleries seem intimidating, with austere interiors, incomprehensible art, and stern-looking staff. But fear not: there’s no dress code, and the staff is perfectly happy for you to have a look around. A gallery hop—along Newbury St. or through the South End’s beautiful SoWa—is an economical way to get some culture and sample Boston’s busy contemporary-art scene. It also makes a fun way to make a cheap date feel classy—squeeze in a few galleries between a Restaurant Week lunch and a mini massage. Check newspapers and the Boston/New England Gallery Guide. Stop by for exhibit openings, and you’ll even get free food and drink.

Customs & Etiquette

Table manners

In the US, good table manners means quiet eating. Loud chewing, talking with food in your mouth, or slurping are seen as rude, and burping or flatulence is not seen as complementary to the chef. Servers at sitdown restaurants usually expect to be tipped 15-20%.

Public behavior

Dress in the US tends to be more modest than in Europe. Toplessness, particularly in women, should be avoided. Many establishments will require a customer to wear a shirt and shoes. The most acceptable forms of public affection are hugging and holding hands; kissing in public will usually draw some glances. Although most cities are tolerant of homosexuality, gay or lesbian couples should be aware that they may receive unwanted attention for public displays of affection, especially in rural areas. Also, note that many American will say “see you later” without really intending to make future plans.


One of the most offensive gestures in the US is extending your middle finger at someone. Known as “giving someone the finger,” this gesture is considered not only rude, but obscene. On the other hand, a “thumbs up” gesture is a sign of approval and a widely recognized signal for hitchhiking, which Let’s Go does not recommend.

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