Boston is a hip, edgy, cultural gem of a city masquerading as a quaint, quintessentially American (with strong Irish undertones) town. It’s bite-sized enough to walk or bike most places, and if the weather’s eliminated that from the mix, the T — the public transpo solution Bostonians love to hate — has got you covered.
A mecca for students, the city is abuzz with intellect, artsiness, and a freedom-trailing, dirty-water-loving, pioneering spirit all its own. Come for the cobbled streets, the oil-burning street lights, the spooky old stone cemeteries, and stay for the vibrant energy, the gruff local hospitality, and the unexpected funkiness of a scholarly yet hyper-hip metro area.
The art scene in Boston is legit. With artsy schools like Emerson and Berklee College of Music, the underground art scene vibrates with youthful energy, while the more traditional artistic outlets shine equally as bright. The Museum of Fine Arts (465 Huntington Ave, Boston) has a rich permanent collection ranging from the Baroque to Impressionist, and boasts a pretty killer Asian art collection. The Institute of Contemporary Art (25 Harbor Shore Dr, Boston) is an equally inspiring option for those with a tendency towards the more interpretive.
For the movie buffs, check out the Coolidge Corner Theatre (290 Harvard Street, Brookline) for indie flicks in a classic theatre, and The Brattle in Harvard Square (40 Brattle St, Cambridge) for the best in classic, cutting edge, foreign, or art house films. Check it out around Halloween for some epically timeless horror flicks.
Boston abounds with gustatory delights, from the traditional seafood fare to more eclectic world cuisines. Turkish-inspired Oleana (134 Hampshire St, Cambridge) is a standout favorite with savory spiced carrot purée and sumptuous deviled eggs with tuna and olives. Saloon (255 Elm St, Somerville) in Davis Square has a remarkable whisky selection and a solid American menu, Grafton Street (1230 Mass Ave, Cambridge) is a must for the requisite clam chowder stop, and James Hook (15 Northern Ave, Boston), for a lobster roll only New England can deliver. Despite the ever-present tourist throngs in the North End, the arancini at Galleria Umberto (289 Hanover St, Boston) have been described as “perfect” and the cannoli at Caffe Vittoria (290-296 Hanover St, Boston) are an essential stop downtown. For some hearty Jewish comfort food, don’t miss Zaftigs (335 Harvard St, Brookline) out in Coolidge Corner.
Boston is way more than the Freedom Trail and Faneuil Hall; there are clandestine surprises hiding in every crevice of this red brick city. Art-wise, the Harvard Fogg Museum (32 Quincy St, Cambridge) has a quiet permanent collection that includes the original Bernini molds for the Ponte Sant’Angelo in Rome. The Isabella Stewart Gardner Museum (25 Evans Way, Boston) is an absolute must for any appreciator of priceless artifacts. Ms. Gardner was a consummate patron of the arts, and her collection boasts Dante’s letter opener, among other precious tchotchkes, as well as a Secret Garden-like ambiance that makes for a welcome respite from the bustling city. For a more, err, iconoclastic art experience, check out the Museum of Bad Art (46 Tappan St, Brookline).
Insofar as clandestine watering holes go, check out the members-only Foundation Room behind House of Blues (15 Lansdowne St, Boston), Brick & Mortar (567 Mass Ave, Cambridge) in Central Square for a strong, swanky cocktail, and Drink (348 Congress St, Boston) the second Sunday of the month for Tiki Sundays.
Also, MIT’s basement tunnels are rad if you’re into that sort of thing.
Boston is full of green spaces that boast beauty and a Thoreauvian naturalism year-round. Stroll through the Olmsted Park greenbelt in Jamaica Plain for a wild, forested promenade before reaching Jamaica Pond. While you’re tooting around JP, check out the Arnold Arboretum of Harvard University and satiate your horticultural side. Also in the neighborhood is Allandale Farm (259 Allandale Rd, Chestnut Hill), an organic farm (the only one within the city limits) that churns out delicious produce for local CSAs. On the other side of the Charles, stroll the riverwalk in Assembly Row in Somerville and Mt. Auburn Cemetery in West Cambridge. The esplanade along the Charles is a classic crowd pleaser, too, for a couple-mile walk between the iconic Citgo sign of Kenmore Square and downtown.
Boston is a young town — the enormous student population keeps the city vibrant and the hippie-hipster count high. Allston and Jamaica Plain have the market cornered — Allston with a grungy, college vibe, and JP with a more suburban, subdued feeling. Check out the Lucy Parsons Center (358A Centre St, Boston) in Jamaica Plain, an “independent, non-profit, radical bookstore and community space” run entirely by volunteers. It has a wide swath of anarchist and leftward-leaning literature as well as poetry readings and community events. While you’re in JP, swing by City Feed and Supply (672 Centre St, Boston) for a luscious vegan sando stuffed with organic, local ingredients. On the Cambridge side, find some sweet vintage threads at the Garment District (200 Broadway, Cambridge) (but beware of its flustercluckness around Halloween-time with costume shoppers out in full force), and work up an appetite for the nearby Life Alive (765 Mass Ave, Cambridge), a crunchy feast for the vegan senses.
Boston is not short on bars. Namely Irish bars. The Burren (247 Elm St, Somerville) is a Davis Square favorite complete with Irish trad performances and pub eats, and Matt Murphy’s (14 Harvard St, Brookline) is chill-ish Brookline Village nouveau Irish spot with local Harpoon beer on tap. Also out in Somerville, Brass Union (70 Union Square, Somerville) is a bougie-in-a-good-way “subterranean hideaway” housed in the old Union Square police station, complete with giant Jenga and other lawn games. Eastern Standard (528 Commonwealth Ave, Boston) is a buzzy yet friendly scene in Kenmore that’s perfect for some pre- or post-Sox-game libations, and the Bukowski Tavern (with two locations: 50 Dalton St, Boston and 1281 Cambridge St, Cambridge) has a wicked selection of beers on tap.
For a happening live music scene, check out The Sinclair (52 Church St, Cambridge), Paradise Rock Club (967 Commonwealth Ave, Boston), and The Middle East (472-80 Mass Ave, Cambridge) for diverse lineups of local acts and headliners alike.
A trip to Boston wouldn’t be complete without some stereotypical Bostonian things. Charles Street and Beacon Hill have the whole charming-brownstone-cobbled-street thing down pat. Hit the Cheers Bar (84 Beacon St, Boston) on your way out for a stroll through Boston Common en route to storied Newbury Street. Newbury is worth a walk to check out the many eateries and shops lining the quaint street — Trident Booksellers and Cafe (338 Newbury St, Boston) and Newbury Comics (332 Newbury St, Boston) are favorites. The Boston Public Library Back Bay branch is everything an old scholarly library should be — just grab your tweed blazer and your Wittgenstein reader and settle in under a green study lamp for the afternoon.
And then, of course, there’s Fenway Park (4 Yawkey Way, Boston), the home of hometown heroes the Red Sox, with its famous Green Monster towering above left field.
Cape Cod is the perennial Boston getaway. There are little hamlets peppered throughout the peninsula, but some favorites are Wellfleet, an Atlantic-side village famous for oysters (pro tip: OysterFest is coming up soon on October 15-16) and Provincetown for some LGBTQ fun.