How outdoorsy-minded LGBTQ groups—and solo travelers—get away in New England
Summer may be winding down, but the fun is just getting started.
Fall, after all, is the season that New England does better than anywhere else in the country. So now that you’ve put away your bathing suit and broken out your comfy sweaters, prepare to hit the road and see every nook and cranny of the region in a different, foliage-filled light. Want to meet some LGBTQ friends along the way? We’ve highlighted some unique (and mostly outdoorsy) social groups in each state. Connect with them to see the best of these beautiful destinations—or just hoof it solo, and follow our guide to staying, playing and dining across all six states.
Vermont
Ah, New England. From the mountains to the valleys, and from the sandy seashores to the soothing stillness of forest lakes, there’s so much natural beauty to discover—and since 2014, the Venture Out Project has been helping queer and trans folks explore it all in safe, supportive numbers. While the Project continues to plan beginner-friendly day hikes and overnight excursions across the area, it also recently established its brand-new Basecamp at Beaver Falls—a 40-acre headquarters in Halifax, Vermont—as a permanent location for hosting all sorts of wilderness adventures. The September schedule, for instance, includes a backpacking adventure for plus-size queer folk, while an immersive forest-bathing retreat is on deck for October. Want to plan something private? The Basecamp—compete with cabins, a riverfront beach, golf course, wood-fired sauna and pool-table-equipped “party barn”—can be rented for all sorts of outdoorsy group events. More: ventureoutproject.com
Where to stay: If roughing it in the woods isn’t exactly your style, retreat at the end of the day to The Brattleboro, a gay-owned luxury inn opening in September in (where else?) the artsy valley town of Brattleboro, Vermont. Tucked away on 32 acres of woods with its own private pond, the property boasts an infrared sauna as well as a chic, adults-only pool and hot tub, where chilled martinis and fancified s’mores can be summoned with just a tap of your smartphone. The inn’s “pillow menu,” meanwhile, lets you choose a luxury-linen-cased cushion designed specifically for your sleeping style.
Where to eat: A fine-dining institution in downtown Brattleboro (and longtime favorite of the region’s gay community), Peter Havens is the place to splurge on a gourmet dinner of local, in-season ingredients or kick back and snack on oysters at the dedicated raw bar, Brattleboro’s first.
What to do: Do you prefer to enjoy Mother Nature au naturel? For as long as the fall weather is warm, doff your clothes at Rock River in nearby Newfane, where a secreted-away nude beach—reached by a short hike—is a decades-running destination for gay skinny-dippers (and stewarded by a newly formed preservation society that respects that heritage).
Rainy day tip: Besides housing a hotel upstairs, Brattleboro’s four-screen Latchis Theatre is a bona fide art deco landmark showing first-run films and hosting live cultural events, such as a recent run of Wagner operas.
Rhode Island
You’d be hard-pressed to find a more beautiful place to go biking than Block Island. After all, even though this 10-square-mile speck of land off the coast of the Ocean State is reached by ferry in less than an hour, it still feels like a totally undiscovered gem—summer tourists are usually too busy hoofing it to the Massachusetts islands of Martha’s Vineyard and Nantucket. Hence the untrod nature you’ll enjoy when biking the miles of Block Island trails that wind by seaside bluffs, salt ponds, historic lighthouses and many more picturesque points of interest. The best way to see it all? In the company of the Chiltern Mountain Club, a 1978-founded social group for outdoorsy LGBTQ folks, which will pedal its way through a 15-mile ride here on Saturday, September 24 (followed by a sneaker-powered hike on Sunday). It’s the perfect opportunity to discover Block Island, but if you can’t make it, take note: Chiltern plans up to 30 outings a year throughout New England. More: chiltern.org
Where to stay: From Provincetown, Massachusetts to Portsmouth, New Hampshire, the Lark Hotels portfolio of properties has spread ultra-cool, modern style and unique amenities across New England. Lark’s Block Island Beach House, though, might be its most exciting entry yet: It offers the only beachfront hotel rooms on the island, many with balconies and patios. The vibe? Breezy, whether you’re lounging around the pool, on the front porch, or at the open-air Beach Bar where cocktails such as fruity rum punch flow on draft.
Where to eat: Block Island may feel a world away, but the flavors are unmistakably global at Eli’s Restaurant. Chef Erika Monat’s menu is a well-stamped passport to sushi-grade-tuna-topped nachos, lamb ragu over lemon-thyme fettuccini, and other adventurous plates that lure locals and tourists alike. Take note, though: This intimate bistro doesn’t accept reservations.
What to do: Meet up with LGBTQ islanders and visitors during Block Island Pride (September 15–18). Produced by the folks behind Queer Block Island, this second annual installment will feature dance parties and a drag brunch, tarot readings, movie nights, a nature walk and much more.
Rainy day tip: If the clouds roll in, curl up with a copy of “Fall Love,” Anne Whitehouse’s 1980s-set novel about bisexual bohemians exploring romance and relationships on Block Island.
New Hampshire
Most New Englanders hate to rush winter—except, that is, for skiers. Even before all the fall leaves have fallen from the trees, some of us are already daydreaming of slaloming our way down snow-covered slopes (and, importantly, reserving our weekend resort stays while there’s still availability). Just look at the members of Outryders: Every November, New England’s largest LGBTQ ski and snowboarding club hosts its season kickoff party in Boston, then launches straight into an action-packed schedule of day trips and overnights to mountains throughout the region. Although the 2022-2023 lineup of outings was still unannounced when this issue of Spirit went to press, history suggests that the crew will be heading back to several sites in the heart of the Granite State’s gorgeous White Mountains region, including Cannon, Loon and Bretton Woods. Don’t miss the chance to get away with other gays to these winter wonderlands—then again, it never hurts to head up early for some fabulous autumn leaf peeping on your own. More: outryders.org
Where to stay: Husbands Eddie Bennett and Christopher Bellis proudly display a Pride flag beside the front door of the Cranmore Inn in North Conway, New Hampshire. If that sight wasn’t welcoming enough, you’ll find thoughtful, old-fashioned hospitality once you step inside—as well as a more forward-thinking commitment to sustainability: The 1863-built hotel has been retrofitted to generate half its electricity through solar power. The Cranmore is right in the heart of the White Mountains region, so it’s a perfect place to stay during fall foliage season, but if you want to look ahead, mark your calendar for January 3–5, when the inn will offer special “Pride Ski Weekend” packages that couple overnight accommodations with lift tickets at area mountains.
Where to eat: Like pizza? You’ll love it when it comes from Flatbread Company. Not only does the North Conway restaurant top its wood-fired pies with everything from homemade sausage to mango BBQ sauce, but it is one of the major sponsors of the White Mountains Pride, fostering LGBTQ community in rural New Hampshire since 2019.
What to do: Hiking under colorful forest canopies has to be the ultimate experience in the fall. Since we’re looking ahead, though, keep your eyes peeled for the Ice Castles in North Woodstock, New Hampshire to announce their weather-dependent opening date. As soon as the temperature drops, these striking, majestic sculptures shoot up, illuminated in every color of the rainbow—and trust us, tickets go fast.
Rainy day tip: Ooh, stormy nights are the perfect time to spook yourself silly at Jean’s Playhouse in Lincoln, New Hampshire. For two weekends in October, the theater produces “Ghost Light,” an immersive show that is part haunted house, part live show.
Maine
The fall is a fantastic time to explore the great outdoors in New England—that said, sometimes you’re looking for a getaway that offers the best of city and country life. That’s when Portland should hop to the top of your list: The most populous place in the Pine Tree State combines the charm of a historic Atlantic-side seaport with the amenities of an urban center many times its size (the restaurant scene, in particular, is nationally renowned). At the same time, it is also surrounded by nature preserves, many miles of coastline for cruising by car or boat, and other sites of natural wonder just outside city limits. After you’ve done all that sightseeing, though, head back downtown and hook up with the party animals of Guerilla Queer Bar Portland. Every month, the collective of cocktail lovers chooses a different venue to descend upon en masse—from the Portland Zoo’s on-site craft beer bar to the ’60s-retro rooftop of 20-lane Bayside Bowl. More: instagram.com/gqb.portland.maine
Where to stay: Extra, extra! Read all about the Press Hotel, a buzzy boutique property in the former headquarters of Maine’s largest newspaper. As you might expect, that’s a running theme throughout the seven-story space—from the massive decorative installation of 62 antique typewriters to the lobby’s News Room lounge and Inkwell, an on-site coffee joint where you can relax with java and a game of Scrabble. All that said, a picture is worth a thousand words, so don’t miss the hotel’s permanent art gallery boasting works from established Maine artists of all kinds. Finally, the chic, herringbone rug-covered guest rooms are all equipped with vintage journalist desks, so you can feel properly inspired while writing out postcards.
Where to eat: Spanish for “last night,” Anoche is the kind of restaurant where we’d love to spend every evening. The queer-owned kitchen specializes in Basque Country-inspired small plates, as well as importuned meat-and-cheese boards, plus wines, beers and a wide selection of ciders made from apples near (Maine’s Whaleback Farm Cider) and far (France’s Christian Drouin Poire Acide).
What to do: You can’t visit Portland without taking advantage of its seaside perch. Kayaks, paddle boards and other wave-ready watercraft from Portland Paddle can be rented for guided tours or your own personal cruising around the islands of Casco Bay.
Rainy day tip: There’s always something exciting on stage at the elegant Merrill Auditorium. This fall, in fact, you’ll find standout shows such as “Chicago,” currently tossing jazz hands on its 25th anniversary national tour, and “The Music of Queen,” a Portland Symphony Orchestra tribute to queer icon Freddie Mercury.
Connecticut
When you’re looking to enjoy a restorative constitutional in the Constitution State, take a rejuvenating walk in the woods with the Connecticut Pride Hikers. Since 2010, the outfit has organized fun forested excursions of mostly moderate difficulty, making it easy for just about anyone to join. It’s a collaborative effort, too, with every member of the Google Groups-based effort invited to plan and lead hikes in any part of the state. The somewhat-official “home base,” though, is Sleeping Giant State Park in Hamden, Connecticut, the site of the very first event. The CT Pride Hikers typically traipse the trails at Sleeping Giant during fall foliage season, soaking up the rugged topography of a mountain nicknamed for its resemblance to a snoozing human. While quaint Hamden might be a bit sedate, there’s nothing snooze-y about neighboring New Haven, where a handful of late-night gay bars and cultural attractions await. More: groups.google.com/g/ct-pride-hikers
Where to stay: Even those of us who never thought we’d want to go back to school would be happy to enroll at the Study at Yale, a smart and sophisticated university-associated hotel sited in the heart of New Haven. It features guest rooms boasting sumptuous leather seats and signature seersucker robes. The chic lobby bookshelves boast tomes by Yale-affiliated authors, if you’re looking to curl up with a good read, and you’ll find superb dining at Heirloom Restaurant & Lounge, where the menu of “farm and coastal cooking” includes wood-roasted oysters with vinegar onions, butter and hot sauce, or duck breast with wild rice and sunchokes.
Where to eat: Sink your teeth into the mouthwatering comfort food at lesbian-owned Latin restaurant Barracuda Bistro & Bar. The New Haven favorite culls Spanish, Colombian and other influences, combines them with American comfort food, and comes up with bright ideas like seafood paella and Peruvian chicken, plus creative cocktails made with fresh juices.
What to do: You’ll always find a friendly scene at 168 York Street Café, a historic brownstone that is now home to a pretense-free gay bar with ample rear patio, drag shows hosted by attention-stealing queens and cheap but tasty pub eats.
Rainy day tip: New Haven is full of fantastic indie shops for hiding away from foul weather (and indulging in a little retail therapy). For instance, swing by Strange Ways, where hip, artsy queers flock for quirky pins, patches and other flair (plus a smart selection of apparel and curios culled from cool indie artists) at this gay-owned shop with a major online presence and curated storefront for friendly freaks and geeks.
Eastern Massachusetts
Pull on your driving gloves and hit the road for Provincetown. While the gay mecca on the Outer Cape is most popular as a summer getaway, there’s still much to see and do in the shoulder season (and it doesn’t hurt that hotel rates plummet once the crowds start to thin). In particular, this is when the motorheads of Yankee Lambda Car Club high-tail it to P’town for the annual invitational car show, held this year from September 16–18. Yankee—the New England chapter of Lambda, a national organization for LGBTQ auto enthusiasts—plans monthly events throughout the eastern part of the state, but the Provincetown weekend is always the yearly highlight. The 2022 installment, dubbed “Wicked Piston,” will include a parade through town, a car show at the Pilgrim Monument and plenty of opportunities to mix, mingle and talk mechanics with other lovers of classic cars, muscle cars and other freshly waxed hot rods. More: yankeelcc.com
Where to stay: Provincetown’s quieter months are the perfect time to splurge on a stay at the Crowne Pointe Hotel & Spa. Why? Not only does the luxury resort has sumptuous accommodations, arranged throughout six bungalow-style buildings that surround a courtyard pool, but you’ll have a world-class spa at your finger (and toe) tips. Book a deep tissue couples massage, cleansing facial or restorative reiki chakra balancing, then soak up the steam room, Himalayan salt sauna or mineral soaking tub before returning—far more rested—to your comfy quarters.
Where to eat: There’s a handful of restaurants in Provincetown that stay open year-round, and among them, Napi’s is somehow both a half-century institution and an under-the-radar gem—maybe because it’s tucked off a side street away from bustling Commercial Street. Look for the elaborate stained glass art over the bar where locals clink cocktails and dig into global eats, from Thai chicken and scallops to Portuguese seafood bouillabaisse.
What to do: In the mood for wine? Try some Cape Cod-grown grapes in a glass at Truro Vineyards in neighboring North Truro. The beautiful property offers tours and tastings into fall, and it continues to host special events like the annual Grape Stomp on September 18 and band-filled Vinegrass Music Festival on October 2.
Rainy day tip: When dark clouds roll in, roll over to the Provincetown Art Association and Museum. Besides the permanent collection and special exhibitions, there’s the annual PAAM Party on October 1, a gala celebrating the legacy of P’town, America’s oldest artist colony.
Western Massachusetts
The Berkshires are beautiful. This mountainous region of the Bay State is also big, though, which can make it difficult to discover every nook, cranny and charming enclave tucked between all those stunning peaks and dramatic valleys. Need some help calibrating your geographic gaydar? Check out LGBTQ+ Berkshire Adventures, a Facebook group where members share the best queer-friendly things to do (and places to go, and sights to see) in Western Mass. Less an official organization than a loose collective of virtual-bulletin-board contributors, these adventure-seekers share all kinds of local secrets: from awesome ongoing events—such as the monthly Mad Juicy comedy showcase in Northampton, hosted by queer standup and DJ Ang Buxton—to one-off experiences like the Pride Night held at the Massachusetts Museum of Contemporary Art in North Adams. More: facebook.com/LGBTQ+ Berkshire Adventures
Where to stay: At Hotel on North in Pittsfield, Berkshires bohemia meets industrial chic. Guest rooms have cloud-like beds and Victorian-inspired furnishings with exposed brick accent walls, and you’ll also find a full fitness center, art gallery, boutique selling local-made wares and more. Hungry? Just head downstairs to Berkshire Palate, the hotel’s restaurant, serves up fantastic American cuisine such as duck breast with blueberry demi and farm squash with blistered tomatoes, purple peppers, and pine nut chimichurri.
Where to eat: If you only fly by one restaurant, make it Blue Heron in the small town of Sunderland. The lesbian-owned fine dining legend housed inside the old town hall, a unique and elegant setting that actually hosted out “Glee” actress Jane Lynch’s wedding. It’s no surprise that she was smitten with the outstanding New American cuisine, made with ingredients sourced from over two-dozen small local farms.
What to do: For nightlife in the Berkshires, Northampton is definitely your best bet. Nearly every bar in town is queer-friendly, but standouts include Bishop’s Lounge (if you’re in the mood for straight-up dancing to DJ tunes), Ye Ol’ Watering Hole (a comfy dive known for its display of 4,000 beer cans), and Fitzwilly’s, a favorite pub for women in town.
Rainy day tip: Following a major renovation, the Emily Dickinson Museum in Amherst reopened in August. That’s just in time for the legendary poet’s birthplace and home to host its annual “Tell It Slant Poetry Festival,” full of workshops, panels and readings that attract literati from around the world.
