New England Gay Weekend Getaways - Best Weekend Trips from Boston

Politically progressive Boston is not only the capital of the first state that legalized gay marriage, it's also within a three-hour drive of countless gay-friendly resorts and vacation destinations, from the soaring mountaintops of Vermont and New Hampshire to the charming coastal hamlets of and Rhode Island - and don't forget other cool getaways elsewhere in Massachusetts, from the Cape to the Berkshires. Here are some great destinations that make a perfect gay-friendly retreat from Boston.

Thinking about tying the knot on the Cape? Check out the Provincetown Gay Wedding Guide.

  • 01 of 10
    Autumn mist in the village of Tyringham in the Berkshires

     DenisTangneyJr / Getty Images

    In the hilly, rural western reaches of Massachusetts, you'll find the Berkshires, a region famous for its vibrant summer performing arts programs (from Tanglewood Music Center to Williamstown Theatre Festival) and year-round museums, including MassMoCa and the Norman Rockwell Museum. In fall, this is one of the Northeast's prime areas for admiring the fall foliage. Towns like Lenox, Great Barrington, Stockbridge, and Williamstown are rife with magnificent old country inns and restaurants, and former mill towns like North Adams and Lee have also become rather gentrified of late. The Berkshires region is about the same distance from Boston and NYC, making it a good rendezvous point for friends from either. Distance: 125 miles (2 to 2.5 hrs)

  • 02 of 10
    The lighthouse perched on the edge of Aquinnah Cliffs, formerly Gay Head Cliffs, ranks among the most iconic Martha's Vineyard landmarks.

    Andrew Collins

    GLBT travelers who venture to Cape Cod often keep right on going to the end of the road, Provincetown. But the rest of the Cape is quite charming and completely gay-friendly, as are the two famous islands accessed by ferry or plane from the Cape, Nantucket and Martha's Vineyard. The latter has gained increased cachet lately as both Presidents Clinton and Obama vacationed here. The 100-square-mile island offers a mix of bustling small towns like Oak Bluffs, Vineyard Haven, and Edgartown, and more rural and remote areas, where you're apt to find great hiking, biking, beaches, and lobster shacks. Far less crowded and pricey in the off-season, Martha's Vineyard is quite mild in spring and fall. Distance: 80 miles (3 hrs with ferry crossing)

  • 03 of 10
    Newport, Rhode Island

    Andrew Collins

    Prior to the American Revolution, the gilded seafaring city of Newport ranked among the five largest metropolises in the New World. Then in the late 19th century, having grown little in 100 years, Newport became a summer destination favored by some of the wealthiest industrialists in American, from Vanderbilts to Astors. This upscale town with a stunning setting on Aquidneck Island is still a favorite getaway of the rich and famous, but Newport's bounty of fine hotels and restaurants appeals to a broader spectrum. And though it's an aesthetically conservative place, it's quite popular with GLBT travelers. Many of the city's massive, venerable mansions are now open for guided tours in this tony sailing enclave. Distance: 75 miles (1.5 hrs)

  • 04 of 10

    Andrew Collins

    A center of education, the arts, and progressive politics in central-western Massachusetts, bustling and relatively affordable Northampton anchors the leafy Pioneer Valley, which extends from Connecticut to the state's tri-border with Vermont and New Hampshire and takes in a series of lovely towns (Greenfield, Deerfield, Amherst) and one hardscrabble city with some excellent museums and a bit of gay nightlife, Springfield. Northampton has long enjoyed a reputation as a favorite place for lesbians to live and visit - it's actually quite popular with gay men, too. Smith College is the small city's cultural hub, and the adjacent downtown abounds with quirky coffeehouses, bookstores, and bars and music clubs. Distance: 100 miles (1.5 to 2 hrs)

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  • 05 of 10

    Andrew Collins

    The tiny seaside village of Ogunquit and Maine's largest city (pop. 65,000), Portland, are two distinct destinations, but they're both exceedingly gay-friendly and easily reached from Boston (and each other). In combination, they make a perfect urban-meets-beach-hideaway vacation. Little Ogunquit is a scaled-down, mellower alternative to Provincetown, with quite a few gay-owned B&Bs, restaurants, and bars, as well as a beautiful beachfront. Just 35 miles north, Portland has a stellar food scene for a city itself, and a charming Old Port district with several notable galleries and boutiques, and the gay-popular historic West End. Portland is also the site of the Southern Maine Gay Pride Festival each June. It's also a good starting point for exploring farther up Maine's scenic coast, toward Rockland and Bar Harbor. Distance: 110 miles (1.5 to 2 hrs)

  • 06 of 10
    Portsmouth, New Hampshire

    Andrew Collins

    A short drive north from Boston, Portsmouth is a small urban jewel along New Hampshire's fairly short stretch of Atlantic oceanfront - it borders Maine and is quite close to the aforementioned communities of Ogunquit and Portland. The city is well-known for its many colonial buildings, several of which are preserved in the historic neighborhood that comprises the Strawbery Banke Museum. The city of 20,000 has a lively downtown overlooking the Piscataqua River and is adjacent to a cluster of islands that contain the small town of New Castle and the historic Wentworth-by-the-Sea Hotel. The gay scene here is low-keyed, with no nightlife to speak of, but this is a charming and welcoming city with several fine B&Bs. Distance: 55 miles (1 hr)

  • 07 of 10

    Andrew Collins

    Just a quick hop down I-95 from Boston, the second-largest city in New England is one of those underrated gems that leisure travelers sometimes overlook, but savvy fans of food, art, live music, and colonial architecture adore. Providence is an important center of education (home to Brown University, Rhode Island School of Design, and Johnson & Wales University among others), and this in part accounts for the sizable, and visible, gay population. A bit less button-down than Boston, Providence also has a small but edgy gay nightlife scene. Fall and spring are the prettiest times to visit this hilly city, home to one of the best "Little Italy" neighborhoods in the country. The city hosts Rhode Island Pridefest in June. Distance: 50 miles (50 min)

  • 08 of 10

    Andrew Collins

    Although its at the alluringly remote tip of Cape Cod, the world-famous gay resort town of Provincetown is relatively easy to reach from Boston, either by car year-round or via high-speed ferry from spring through fall. This historic fishing village (the Pilgrims stopped here in 1620) developed a Bohemian following as a colony of artists and theater buffs toward the end of the 19th century and has been a favorite destination among lesbians and gays ever since. The beaches of nearby Cape Cod National Seashore are among the least spoiled in the Northeast, and lively Commercial Street abounds with galleries, gay bars, fine restaurants, and gay-owned guest houses. Even in winter, P-Town is quite charming. The town is also an ideal one for planning a gay weddingDistance: 110 miles (2 to 2.5 hrs)

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  • 09 of 10

    Andrew Collins

    The entire state of Vermont offers countless charms, but from Boston your best bet is to focus on the closer lower half of the state, which takes in such fabled ski areas as Killington (pictured below), Stratton, and Mt. Snow, as well as a seemingly endless supply of inviting country towns and hamlets. Excellent bases - with plenty of charming inns and romantic restaurants - include Manchester and Woodstock. Smaller villages like Arlington and Grafton are highly scenic. This largely rural, environmentally conscious state was the first in the country to pass gay civil union legislation (full gay marriage rights has since followed), and GLBT travelers will encounter warm hospitality throughout the region. Beautiful Burlington, the state's largest city, is only a couple of hours farther north. Distance: 150 miles (2.5 to 3.5 hrs)

  • 10 of 10
    White Mountains

    Andrew Collins

    Northern New Hampshire's White Mountains contain the highest peaks in the Northeast and are a popular playground for hiking and biking in summer, leaf-peeping in fall, and skiing and snowshoeing in winter. The historic village of Bethlehem is home to Highlands Inn, one of the most acclaimed lesbian resorts in the country. Although the region is both isolated and somewhat conservative (in a libertarian sort of way), GLBT travelers will find plenty of kindred spirits among the romantic inns of Jackson and Franconia, and such renowned ski resorts as Bretton Woods, Loon Mountain, and Waterville Valley. Be sure to visit Mt. Washington's historic Cog Railway, and drive the scenic Kancamagus Highway (pictured below). Distance: 120 miles (2 hrs)