Summer may signal the end of high season at New England’s beach resorts, but September and October are the perfect months for visiting the region’s largest metropolis, Boston, along with its smaller neighbors, Cambridge and Somerville. At this time, the city comes alive as students return to the area’s many colleges, the leaves turn bold shades of orange and crimson in gardens and parks around town, and restaurants and bars with terraces and sidewalk seating entertain fans of alfresco dining for a few more weeks of warm weather.
Here’s a look at one of the nation’s gay-friendliest destinations, with a particular eye toward what to see during the fall months. But you’ll find tips here on things to do, cool inns and hotels, and hip dining and nightlife that should come in handy no matter what time of year you visit.
The South End
This handsome neighborhood of narrow, tree-shaded streets lined with Victorian bow-front, redbrick townhouses has steadily evolved over the years into one of the city’s favorite destinations for an afternoon stroll, whether to admire the architecture, duck into tony boutiques, or seek out trendy neighborhood bistros and cafes. This upscale district is very much the heart of Boston’s gay scene, and it’s home to several long-running LGBT nightspots – the endearingly dive-y Boston Eagle, the classic dance club and video bar Club Café (clubcafe.com), the friendly sports bar Fritz (fritzboston.com).
A favorite pastime around here is dining out, with most of the top restaurants along the main thoroughfares of Tremont Street, Washington Street, and Columbus Avenue. Longtime favorites of the gay community, like Franklin Café (franklincafe.com) and Tremont 647 (tremont647.com), are as popular as ever both for dining and drinking. But in recent years, quite a few other culinary stars have helped shine a light on the neighborhood, including Coppa (coppaboston.com), where you’ll find superb charcuterie and cheese plates, wood-fired pizza and wines by the glass; and newcomer Estelle’s (estellesboston.com), which earns raves for its updated take on Southern cuisine, from crispy catfish burgers to buttermilk fried chicken.
Jamaica Plain
Slightly out of the way lies Jamaica Plain, or JP as it’s affectionately known, a few miles southwest of downtown Boston, in a relatively residential part of Boston that tourists sometimes miss. Especially if you’re visiting during the fall foliage season, this funky, progressive neighborhood with a solid lesbian following merits a visit.
Boston’s famed Emerald Necklace—a string of dozen green spaces laid out by eminent 19th-century landscape architect Frederick Law Olmsted—has several significant sections in Jamaica Plain, including Franklin Park (with its historic zoo), Arnold Arboretum (with 280 acres of plants and trees connected by well-marked paths), Jamaicaway (a tree-lined parkway), and Jamaica Pond. You can continue along the Emerald Necklace visiting the other linked parks, including Olmsted Park in Brookline, the Riverway, the Back Bay Fens (where you can access the outstanding Isabella Stewart Gardner Museum and the Museum of Fine Arts), Commonwealth Avenue Mall, and finally the Public Garden and Boston Common. The entire string of parks is about 10 miles (and popular as a biking route), but it’s easy just to choose a few portions of it and explore those on foot. All of the Jamaica Plain parks are great for strolling and jogging.
Cambridge and Somerville
These two neighboring cities just across the Charles River from Boston are sometimes considered mere extensions of their larger neighbor, but each has a great deal going for it and sizable LGBT populations. Cambridge (cambridgeusa.org), with about 106,000 residents, is most famous has the home of Harvard University and MIT, and indeed these world-renowned educational institutions are worth visiting, especially the many esteemed attractions related to the arts and sciences—the Harvard Art Museums, Peabody Museum of Archaeology & Ethnology, Museum of Science, MIT Museum. On a sunny September day, it’s a pleasure simply to walk through verdant Harvard Square, or on a path fringing the Charles River.
You’ll also find quite a few performance spaces, from comedy improv to alternative music to modern dance. Check out the American Repertory Theater (A.R.T.), where on Saturday nights Club Oberon (cluboberon.com) stages the queer-fabulous Donkey Show, a wildly entertaining disco extravaganza complete with hot go-go dancers.
Cambridge has some particularly dynamic neighborhoods for exploring, among them diverse Central Square, with its live music venues and affordable ethnic eateries, and student-driven Porter Square, where, particularly along Massachusetts Avenue, the laudable dining options are many. Harvard Square is the hub of the eating action, but all throughout Cambridge, you can find plenty of inviting places to knock back local microbrews and feast on excellent food.
Among the favorite ethnic restaurants in Cambridge, keep an eye out for the Maharaja (maharajaboston.com) for well-prepared Indian cuisine in an elegantly decorated dining room, Thelonious Monkfish (theloniousmonkfish.com) over in Central Square for sushi and mod Asian-Japanese fare, and Koreana (koreanaboston.com) for Korean fare. Cambridge is also at the forefront of locavore-minded, seasonal cuisine, with some true destination dining notables. T.W. Food (twfoodrestaurant.com) has helped to lead this charge with its farm-to-table menu. The Sunday jazz brunch is a lot of fun. Another gem, near MIT, is Salts Restaurant (saltsrestaurant.com), which turns out well-crafted French-inflected contemporary food, from bergamot-cured ocean trout to whole roasted boneless duck for two.
Somerville, with a population of about 77,000 and a location just north of Cambridge, is primarily residential, but it’s home to several cool dining and nightlife options, especially around bustling Davis Square, where you’ll find the inviting Spoke Wine Bar (facebook.com/SpokeWineBar), which serves commendable food and vino well into the evening. Hipster-favored Diesel Café (diesel-cafe.com), a worthy source of sandwiches, salads breakfast fare and craft coffee, puts an emphasis on local provisions. Bergamot (bergamotrestaurant.com), a short walk from Cambridge, is one of the hottest tables in Somerville, thanks to the super globally inspired modern American fare, the nightly $39 three-course dinner special, and top-notch cocktails (plus great beer and wine lists).
Where to Stay in Boston and Cambridge
One of the most fascinating hotel adaptations in the country, the gay-friendly Liberty Hotel (libertyhotel.com) is built around what had been the Charles Street Jail, an imposing granite building that dates to 1851. Since its masterful architectural conversion in 2007, this luxe 298-room property by the Charles River has become a desirable overnight destination, its rooms with huge windows overlooking the river, and its bars and restaurants drawing a see-and-be-seen crowd, especially Clink, where you can dine amid the grillwork of the former jail cells.
The South End’s gay-owned Encore B&B (encorebandb.com) is a romantic but reasonably priced option; the redbrick townhouse on a tree-lined street has four stylishly appointed rooms with private baths, flat-screen TVs, and plush bedding. With rates starting at under $100 for a room with shared bath (rooms with private baths don’t cost too much more), the neighboring Adams B&B (adamsboston.com) and Oasis Guest House (oasisgh.com) are couple of the top bargains in the city. These gay-owned properties enjoy a great location by Fenway and the Back Bay, and have compact, simply furnished rooms, plus outdoor and indoor common areas; if you just need a clean and safe place base for exploring, these are a good bet.
Pet-friendly boutique-hotel brand Kimpton has a couple of dapper properties in downtown Boston: Nine Zero (ninezero.com) is situated by the Boston Common and has 190 super-swanky rooms, including several urbane suites with distinct themes (note the carved deer heads in the Lodge Nouveau Suite). Kimpton’s Onyx (onyxhotel.com) is close to Faneuil Hall and the North End and has 112 boldly decorated rooms, each with iHome entertainment systems.
In Cambridge, consider Kimpton’s dapper Hotel Marlowe, whose 236 handsomely furnished rooms have animal-print carpets and opulent velvet fabrics – the spacious suites are especially memorable, with their floor-to-ceiling windows and telescopes, perfect for ogling the Boston skyline just across the river. Guests can take out complimentary kayaks for a paddle on the Charles, and the restaurant, Bambara, serves delicious Italian-accented modern New England fare.
A convenient Harvard Square location accounts in part for the tremendous popularity of the Charles Hotel (charleshotel.com), a light-filled 295-room hotel that’s home to the acclaimed restaurants Henrietta’s Table (for regional American) and Rialto (modern Italian), two popular bars, and a terrific urban spa, Corbu. The hotel lends guests complimentary bicycles to pedal along the nearby Charles riverfront. The nearby Hotel Veritas (thehotelveritas.com) has just plush but intimate rooms, with commissioned artwork by local talents, Turkish bath linens, iPod docks, and plenty of other perks—this is a lovely place to stay if you’re seeking a more laid-back, boutique hotel with exceptional one-on-one service.
Andrew Collins is the editor in chief of the LGBT travel magazines OutAloha and OutCity, and he covers gay travel for the website GayTravel.About.com. He can be reached care of this publication or at OutofTown@qsyndicate.com.
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