No other major city in America is trapped in so thick a stereotypical aspic as Boston. We’re the city of dropped r’s and weathered Red Sox caps, the home of the Kennedys and St. Paddy’s Day, the nation’s most territorial residents and its most obnoxious sports fans.
Some of these generalizations are earned, some are grossly unfair, and some are long past their expiration dates—green beer is not really a thing, even in mid-March—but all of them obscure the long, inspiring life of the city and its surrounds.
So set aside your lobsta’ and jimmies, cycle that “Free Brady” jersey to the back of the closet for a bit, and let’s celebrate the things that make Boston and its region—together, the birthplace of America—worth loving so much. Wicked.
1. A huge mix of geography and people. Greater Boston’s 4.73 million residents are as profoundly diverse as the variegated mass of geography over which they’re spread—from dense urban neighborhoods, suburban redoubts, exurban bedroom communities, and downright rural pastorals—in its dozens upon dozens of municipalities. Nearly half of the city of Boston itself is nonwhite, and the 56,000-plus students in its public schools speak 74 languages.
2. Fall’s first days. Nowhere else in the country does a crisp autumn day quite like Boston. (And soak it up, because there’s no denying that the winters here are terrible.)
3. Glimpsing the skyline from the Red Line as it goes over the Longfellow Bridge. The Pru and 200 Clarendon—and now One Dalton—dominate the unforgettable forest of buildings. Extra wow factor if the leaves are changing along the Esplanade.
4. Sports, and sports culture. Not only is Boston the nexus of franchises that have won countless—countless!—professional world championships, but it’s also home to the world’s most famous marathon and a number of athletic shrines.
5. “I’m from Boston” can mean you’re from Somerville or Lynn. The area’s high density means municipal borders tend to bleed into one another. It can all seem like just one big city—and it almost was—so it’s often just easier to tell outsiders you’re from Boston.
6. Strolling the Rose Fitzgerald Kennedy Greenway. The 17-acre ribbon born of the Big Dig that snakes through much of downtown Boston is one of the nation’s most prized linear parks. And it’s full of hidden gems.
7. West Roxbury vs. Roslindale. The (usually) friendly neighborhood rivalry is the most enduring in the region.
8. Fenway Park. The nation’s oldest Major League ballpark is the home of the Red Sox, the Green Monster, and an eighth-inning chorus of “Sweet Caroline.”
9. Boston Public Library’s central branch. The Beaux Arts-Renaissance Revival hybrid, which was completed in 1895, routinely shows up on lists and in articles of the most beautiful libraries in the U.S.—and rightfully so.
10. The quaint cobblestones and Federal architecture of Acorn Street. They don’t call this Beacon Hill run one of the most beautiful streets in America for nothing.
11. The Harborwalk. The string of parkland edges Boston in an almost continuous 43-mile run that includes ample opportunity to amble waterside and to take in any number of spectacular views.
12. We’re the most walkable city and metro region in the nation. Bar none.
13. Deer Island Treatment Plant. The engineering marvel that sorts, cleans, and collates waste for the Boston region—one of the largest urban sewage plants in the nation—sits amid several pastoral acres on a peninsula on the Winthrop–Boston border. Go for a tour of the oddly fascinating facilities, and stay for a picnic.
14. Squares. No urban area in America uses “square” as frequently and as liberally in its geography as Boston. Squares sometimes denote neighborhoods, though oftentimes they honor an individual or a milestone.
15. The running commentary around Boston City Hall. People either love or hate the 50-year-old Brutalist complex—there is no middle ground.
16. The Harbor Islands. Officially, the Boston Harbor Islands National Park area consists of 34 islands and mainland parks, but the real highlight is the eight islands accessible to the public via seasonal ferries. (Another several are accessible from private boats or charters.) There is a ton to do and see on the islands, which are all relatively close to downtown Boston.
17. South Station. Sure, it can be a headache to navigate, and the noise can be ear-splitting, but New England’s busiest train and bus hub is right there in the middle of Boston—unlike counterparts in many other cities—an accessible and vibrant cord on the municipal guitar.
18. Repurposed parking garages. So many one-time hulking carparks are seeing new life as major mixed-use developments that include much-needed housing.
19. Federal architecture. The first architectural style born in the United States is found throughout downtown Boston, particularly in the works of 18th-century starchitect Charles Bulfinch, including the Massachusetts State House.
20. Henry Hobson Richardson. The 19th-century architect’s works are everywhere in his adopted region. Start with Trinity Church in Copley Square and go from there.
21. These old houses. The Boston region is home to some of the oldest intact houses in America, including the Fairbanks House in Dedham (circa 1631) and the James Blake House in Dorchester (circa 1661).
22. These new buildings. It’s not all old stuff; Boston boasts architectural gems from the late 20th century, too, including works by Walter Gropius, Le Corbusier, Josep Sert, I.M. Pei, Frank Gehry, and more.
23. The U.S.S. Constitution. The world’s oldest commissioned battleship, launched in 1797, remains docked in the Charlestown Navy Yard and is open for tours.
24. The triple-decker. The three-story apartment buildings are a staple of Boston-area architecture and more influential than most people realize: They grew from an effort a century or so ago to pivot away from urban tenements.
25. Jamaica Pond. The phrase “urban oasis” is sometimes overused in writing about cities, but this 68-acre pond and its surrounding greenery is just that.
26. Bunker Hill Monument. “A few more such victories would have shortly put an end to British dominion in America.” So commented the commander of British forces following the Battle of Bunker Hill in June 1775. It was a technical win for the Brits, but the colonialists had inflicted quite a bit of damage. The 221-foot obelisk to their achievement opened in 1843, and is surrounded by terrific parkland; there’s a great Bunker Hill museum across the street.
27. The T is the oldest subway system in the Western Hemisphere. Take that, New York!
28. Ogling all nature of wonders at our world-renowned museums. From the Museum of Fine Arts and the ICA to the Museum of Science, the Boston region has some of the best museums in the country.
29. Along with a host of lovable, unusual ones. That includes one of the last surviving anatomy and pathology museum collections in the country—because not every museum has to be world-rattlingly famous to warrant attention.
30. The courtyard at the Isabella Stewart Gardner Museum. The prime attraction of the beloved Willard T. Sears–designed complex dating from 1901 is its walled-in courtyard meant to reflect the love of horticulture of the museum’s namesake. It’s plush year-round with seasonal blooms.
31. The Hood Milk Bottle. The 40-foot wooden replica outside of the Children’s Museum doubles as an ice cream stand.
32. Driving through the harp strings of the Zakim Bridge. And especially catching the iconic 745-foot, cable-stayed connector when it’s illuminated.
33. Richly significant churches. Including the Old North Church in the North End (“One if by land, two if by sea”), Trinity Church and the Old South Church in Back Bay, and Twelfth Baptist Church in Roxbury—where a young Martin Luther King Jr. ministered. (At some point soon, the city and its nonprofit partners will develop a major monument on Boston Common to honor the civil rights leader and his wife, Coretta Scott King, who met while living here.)
34. Our leaders in the public and private sectors take climate change seriously. Local governments and private stakeholders, including business leaders, have not been shy about trying to mitigate the effects of climate change, in particular rising sea levels.
35. Proximity to Portland. Amtrak’s “Train to Maine” can drop you there in two hours. The drive isn’t unpleasant either.
36. The Return of the Swans. Every early spring for three decades now, a pair of swans returns to the Public Garden lagoon from their winter lodgings at the Franklin Park Zoo—and the entire Boston area cracks a smile.
37. Bike shares. They’re everywhere now.
38. T stops called Maverick and Wonderland. And they’re on the same (Blue) line.
39. The Berkeley Building’s weather reports. The 65-foot mast of the 26-story Back Bay building gives the weather forecast—and indicates whether Red Sox games have been canceled due to inclement conditions—through changing colors.
40. We’re America’s unofficial sneaker capital. Converse, New Balance, and Reebok all have their corporate headquarters within city limits (and Puma is building its HQ in Somerville). The New Balance HQ looms like a spaceship over the turnpike on the city’s western edge.
41. Taking in a concert or movie at the Hatch Shell. The Charles River Esplanade venue is famed for its free shows and laid-back vibe.
42. The Freedom Trail. The 2.5-mile line of red bricks promises more than 250 years of history—and it delivers, including stops at 16 nationally significant sites.
43. No grid? No problem. Boston and much of the region is not laid out on a grid, more closely resembling some kind of municipal spaghetti. Why? It has to do with the age of the area and its charming stubbornness.
44. Donna Summer roller disco. Every summer now for five years, Boston pays tribute to its native daughter, the Queen of Disco, with a party in Boston City Hall Plaza.
45. Hometown players. Aerosmith, Boston, the Cars, New Edition, the Pixies, the Mighty Mighty Bosstones, New Kids on the Block (why not?), and others—so many bands and musicians are from here.
46. And the lesser-known punk and hardcore scene of the 1980s remains influential to this day. Fitting for the city that was home to America’s first rebels.
47. All the Revolutionary War stuff. America’s battle for independence from the British Empire commenced in the Boston area. The reminders are everywhere.
48. Hikeability. Not only America’s most walkable city, the Boston area also has a number of hiking options that range from pleasurable ambles to true exertions.
49. Patriots’ Day and Evacuation Day are real holidays. The latter commemorates the battles of Lexington and Concord and the former marks when the British gave up and left—but it’s also the day the Boston Marathon is run, so most people know it better as Marathon Monday.
50. Louisburg Square. This is probably the most charming area of the most charming neighborhood—Beacon Hill—in Boston. Greek revival townhouses as far as the eye can see.
51. Dudley Square. The bustling commercial and transportation nexus of Roxbury has been undergoing a revitalization of sorts the past few years.
52. The thousands of families of plants and trees in the Arnold Arboretum. Landscape architect legend Frederick Law Olmsted designed the 281-acre expanse in JP and Roslindale, and Harvard owns it.
53. Loads of repurposed buildings. Given the age of Boston, it’s probably no surprise that so many buildings have been retooled for second, third, and even fourth acts. But it’s still pretty lovable that—at least in recent decades—the emphasis has been on incorporation and preservation rather than on tearing things down.
54. Blue Hill Avenue. The busy drag through Roxbury and Mattapan is one of the most storied streets in the region, if not the country.
55. Back Bay really was built on a back bay, and a lot of Boston is built on what was once water. Way back, Boston was simply a cluster of buildings and lanes on the slender Shawmut Peninsula, but a series of infills big and small filled out the place.
56. Cambridge’s Bell and Fandetti townhouses. Architects Doug Bell and Gerald Fandetti designed about 20 clusters of townhouses in the People’s Republic from 1973 to 1981, with distinctive features and energy-efficient designs that were particularly bold for the era.
57. The nation’s first legally recognized same-sex marriage was in Cambridge. At City Hall in May 2004.
58. @. The late Ray Tomlinson is credited with inventing modern email in 1971 while working as a computer engineer at Cambridge-based Bolt Beranek and Newman. One of his most lasting innovations was using the @ symbol to identify addresses.
59. The Theater District. The downtown enclave hosts several venues, and the city has generally been reasserting itself as a drama outpost for shows hoping to make the leap to NYC and other bigger stages.
60. Charles River Esplanade. The three-mile-long, 65-acre Esplanade is the perfect spot for strolling and chilling. Plenty of benches, too—but watch out for the geese.
61. We value our artists. One of the most famous squares in the region is named for a painter: John Singleton Copley was big around the turn of the 18th century, and Copley Square is big in Boston today.
62. There is a 12-foot bronze statue of a pear in Dorchester’s Edward Everett Square. When it was conceived in 2007, creator Laura Baring-Gould intended for people to do a double-take, and they do to this day. The 10 smaller bronzes around the pear each deal with an aspect of the area’s history, and so does the pear itself—a breed called the Clapp’s Favorite was developed in Dorchester.
63. Allston Christmas. The annual late August/early September rite of collegians and other young people putting all manner of household stuff on the curb for others to take is not unique to Boston. But nobody does it quite like Allston.
64. People get very excited about new T cars. It’s probably a function of how bad mass transit can be hereabouts, but the kids-birthday-party-like excitement some locals experienced over the new Orange and Green line cars recently is priceless.
65. Wild turkeys. The big birds are especially prevalent in the summer and fall.
66. John F. Kennedy Presidential Library and Museum. The I.M. Pei–designed library and museum in Dorchester’s Columbia Point turns 40 in 2019. It’s a repository for all things JFK, including a permanent exhibit on the former president’s family.
67. Kendall Square. The tech-heavy Cambridge hub is one of the region’s great success stories, one that’s far from complete.
68. Buskers. Especially on the T and especially Keytar Bear.
69. The social media network that changed the planet was born here. A group of Harvard students led by Mark Zuckerberg loosed Facebook on the world from their Cambridge residences in February 2004.
70. The Edgar Allan Poe statue. The writer was famously not fond of his hometown, but Stefanie Roknack’s bronze sculpture, which officials unveiled in 2014, honors him evermore at the corner of Boylston and Charles streets.
71. Old neighborhood names live on. The Ladder District, the Polish Triangle, New York Streets, Area 4, Ten Hills—these and other enclave labels might have been lost to history, but thanks to devoted locals, they weren’t.
72. Harriswood Crescent’s 15 Tudor revival rowhouses. Dating from the 1880s and 1890s, these charmers sit along Roxbury’s Harold Street.
73. You cannot not find things you need. Because there are furniture and vintage shops for all price points here.
74. We’re still a two-daily town. Boston is one of the few American cities that still supports two daily newspapers, not to mention smaller newspapers, news and culture websites (ahem), radio stations, Jim Braude, local TV news, Callie Crossley—and innumerable Twitter and Instagram feeds. Don’t say you weren’t told.
75. Hails to the chiefs. From George Washington to Barack Obama, the Boston area has had intimate links with several of the nation’s chief executives.
76. We love our victory parades. It seems like every few months, there’s a parade through downtown Boston for the Patriots, the Red Sox, or one of our other winningest teams.
77. And Boston Duck Tour boats are now celebrated parade vehicles. Since 2002, our champions have ridden through the streets on the amphibious crafts. (Outside of the celebrations, of course, they’re a great way to see the city’s sights.)
78. Make Way for Ducklings. Robert McCloskey’s 1941 children’s book of the same name inspired Nancy Schön’s world-famous—and justly so—bronze sculpture of a mother mallard and her eight ducklings in Boston Common.
77. Salem. Yes, the North Shore city about an hour north of Boston has plenty of attractions pivoting around Halloween and witches. But there are plenty of other reasons to check it out year-round.
79. Fort Hill Tower. The city restored the Roxbury landmark—aka the Cochituate Standpipe—earlier this decade, leaving the Gothic structure to loom large once more over Highland Park and the surrounding Fort Hill enclave.
80. We really do run on Dunkin’. The doughnut-and-coffee chain, started in Quincy in the late 1940s, is a staple of the Boston-area diet.
81. Getting out of town—and back home—without a car is a breeze. Logan Airport is more accessible via mass transit than a lot of its contemporaries, and South Station has myriad car-free regional connections.
82. Weekending in Western Mass. One of the nation’s most beautiful and fun areas is a mere two hours from Boston by train, car, or bus.
83. The George Washington statue in the Public Garden. The 38-foot-tall statue of the first president—and one-time Boston-area resident—sculpted by Thomas Ball is impressive in scope. It features prominently in photos of the garden and the skyline.
84. The Skinny House. The North End abode, which is a mere 10.4 feet at its widest on the outside and just over 6 feet at its narrowest inside, is one of the nation’s more famous skinny houses—and it’s got a great backstory.
85. The St. Patrick’s Day Parade in Southie is the most famous of its kind in the world.
86. And there’s no other city that Irish immigrants and their descendants have shaped as much as Boston.
87. Dorchester was its own city. And now it’s the largest neighborhood by area in the city of Boston.
88. The monument to the U.S. Army’s first all-black regiment during the Civil War is one of the nation’s most-visited war memorials. Located on the edge of Boston Common, right across from the Massachusetts State House, the 54th Massachusetts memorial is undergoing a major restoration.
89. Hanover Street. The drag that bisects the North End is swarmed with tourists during the warmer months, but it’s one of the better streets for people-watching and casual snacking.
90. Booze. The region is home not only to some of the best breweries, cideries, and distilleries in the world, but to some pretty fantastic, neighborhood-enhancing taprooms and beer gardens as well.
91. Food. Beyond the chowda and oysters, the region boasts some of the nation’s best diners, delis, restaurants, and, heck, food-truck concerns.
92. Easy trips to the beach. The area’s beaches—and we’ll include the North Shore and the upper reaches of Cape Cod—are often underrated, even by locals. They’re great, though, and the proximity can’t be beat.
93. Bocce at Langone Park. There are three courts at the North End park perfect for the Italian lawn game.
93. Strolling in the spring. Whether in parks, along the streets and the plazas, or by the waterways, a stroll is sublime just after the weather has been icy cold—and just before things turn sticky hot.
94. The streets in Back Bay named after English peers. When the neighborhood was conjured from a real brackish back bay in the mid-19th century, the designers decided to name several of its major streets after English dukes, earls, barons, etc.—Arlington, Hereford, Clarendon, and so on.
95. Newbury Street. The eminently stroll-able drag from the Public Garden through Back Bay is perfect for window (and real) shopping.
96. Fluff. A Somerville original.
97. Myrtle the Turtle. The approximately 80-year-old, 500-plus-pound reptile has lived at the New England Aquarium since 1970.
98. Custom House Tower. The 495-foot spire, which architect Richard Peabody based on the campanile in Venice’s St. Mark’s Square, was Boston’s tallest building from its completion in 1915 to the Pru in 1964. It’s still something to see looming over the Greenway.
99. The big dinosaur outside of the Museum of Science. The museum inside ain’t too shabby, either, with its more than 700 exhibits and planetarium.
100. Author, author! The Boston region and Boston proper boast literary pasts few other areas of the world can match. Both have been home to numerous writers of just about every genre—and both host the earthly remains of several.
101. All the movies set in Boston that don’t actually capture it. So much has changed here in recent years, but Hollywood’s idea of the city seems trapped inside a Red Sox cap inside a Southie dive bar. Oh, how we love to hate some of these films.