Travel
4 min

New England’s historic capital

Boston is a vibrant, walkable city

Faneuil Hall is one of the US's premier urban marketplaces. Credit: Greater Boston Convention & Visitors Bureau

If recents events have left you questioning your plans to head to Boston for Pride at the beginning of June, put your doubts aside. The city needs all the love it can get right now and will amply reward your vote of confidence.

Whether for a weekend or a week, Boston brims with energy, style and charm. Sure, since Boston has held court over this corner of the northeast US since the year 1630, history stars, but this pedestrian-friendly city is increasingly less pedestrian, with innovative dining, cutting-edge art and scintillating social scenes now making quite a splash.

Situated seven hours’ drive from Ottawa or just a 90-minute flight from Toronto, Boston makes an easy quick-trip destination for many Canadians. Spring and summer see a slew of jubilant celebrations deck the city calendar, such as the venerable Boston LGBT Film Festival in early May, Youth Pride (bostonpride.org/youthpride) in mid-May, the exuberant Pride Boston (bostonpride.org) in late May/June and the weeklong Harborfest (bostonharborfest.com) spectacle in July.

When the sun comes out, Bostonians take to the grassy lawns of the 380-year-old Boston Common, to the leafy sidewalks below the red-brick row houses of the South End gaybourhood and to beaches such as Revere, with its Victorian bathing pavilions. They stroll, blade or run the 75-kilometre Harborwalk and amble along the Charles River Esplanade. They camp, kayak and carouse on Bumpkin, Nut and other amusingly named Boston Harbor islands. They nestle down on blankets for the numerous outdoor movie nights held throughout the city, pull up chairs at streetside patios and spill out of crammed clubs. It’s a lively, laid-back, livable city.

If it’s your first visit to the city of 625,000 (metro area 4.6 million), you’ll find most must-dos and mainstays can be explored by foot. Stellar strolls include walking the four-kilometre Freedom Trail, through the pedestrian-friendly Beacon Hill and Italian North End neighbourhoods and along the banks of the Charles River. If you want to stay outside, check those off, then lounge in Boston Common or the adjacent Boston Public Garden. Linger at Quincy Market (officially called Faneuil Hall) to stock up on souvenirs, join in some street theatre or outdoor pilates or simply grab a lemonade and people-watch. Visit Fenway Park to catch a Red Sox game. Gaze at Monets then move on to homegrown talent in the four-storey Art of the Americas Wing of the Museum of Fine Arts.

On the north side of the Charles River, Cambridge, home to Harvard and MIT, is as coffeehouse- and bookstore-studded a neighbourhood as you’d expect. Officially a separate city from Beantown, Cambridge has a population of 100,000, more than a quarter of them enrolled in third-level education. The Kendall Square neighbourhood is a high-tech mecca, populated by MIT types. To soak up the ambiance, brunch on burritos or biscuits and gravy at the funky Friendly Toast (thefriendlytoast.net) or experience the academic milieu at Voltage Coffee & Art. For something more substantial, try the southern fare at Hungry Mother. Although the food-truck scene has been slow to rev up in Boston, a fleet of mobile Clover Food Labs is getting the city’s street eats into gear. You’ll find them, serving unusual sandwiches such as chicken fritter or egg ‘n’ eggplant, in locations from Kendall Square to the Aquarium. Both charming and edgy, Central Square sits south of Harvard Square and Inman Square. It’s a hub of live music, comedy and improv and offers a great farmers’ market and a huge variety of restaurants. Try low-key Flour Bakery for a light snack or neighbourhood spot Green Street for something with a bit more bite.

For a longer stay, let your imagination and your itinerary wander away from the more traditional tourist stops. Explore the vibrant Waterfront, with its eateries, wharfs and tourists ducking dive-bombing gulls, then continue on to Fort Point, the site of the original Boston Tea Party. Today tea isn’t the tipple of choice round here; it’s more likely to be an ironic PBR, a Somerville-brewed Jack D’Or or a can of Cambridge’s Audacity of Hops IPA. Formerly industrial blocks are swiftly becoming swathes of art studios and gallery space, such as the 300-artist community FPAC and art, design and craft cooperative Made in Fort Point. It’s the perfect place to stock up on some conceptual art, a one-of-a-kind hand-hammered salad scoop or that organic twig lantern you’ve always wanted. From here, a 15-minute walk will take you to Liberty Wharf, a haven for slick restaurants and even slicker office towers, and to Temazcal Tequila Cantina, where you can pore over the iPad menu, tuck into an entire roast suckling pig, should you so desire, or work your way through the selection of 300-plus tequilas.

Accommodations
The hip, turn-of-the-century Chandler Inn attracts a high proportion of queer guests to its 56 rooms, lured by the friendly service, the modern amenities and its South End location – and the fact that they’ve tucked a gay sports bar called Fritz into the basement doesn’t hurt. The nine-suite Charles Street Inn offers a slice of old-world Boston in an opulent Victorian red-brick in Beacon Hill.

Bars

For a concentrated dose of queer action, head to the South End, the heart of gay Boston. Sample the early-evening oysters, ceviche or Maine crab salad at cocktail lounge 28 Degrees. For some pre-bar sustenance, try such modern American classics as roasted-turkey meatloaf at Franklin Cafe, then head back later for steamed buns from the late-night menu. Other excellent eat-and-drink options include the tiny restaurant/bar Sister Sorrel and kitschy hipster haven Delux CafĂ©. But don’t linger too long over dinner: Boston clubs have a 2am last call.

You can’t come to the South End without hitting the legendary Club Cafe, a cabaret-cum-dance-bar-cum-video-lounge. It attracts a mostly male crowd, but there are monthly women’s nights, called Juicebox, and women are always welcome. Other scene institutions include the cruisy Eagle, also in the South End, bear hangout The Alley downtown, and upscale DBar in Dorchester. Although the South End has its share of gay women, Jamaica Plain, or JP as it’s known, is where a lot of ladies live. Bella Luna Restaurant and Milky Way Lounge comes courtesy of the folks formerly behind lesbian-loved bowling alley and club the Milky Way. This mixed JP institution may no longer offer opportunities to bowl, but ladies still get a lucky strike, with pizza buffets and the monthly Dyke Night.

For map locations and website links to more than 150 area places of interest see our gay Boston listings pages.