Live Here? Go There: 5 Road Trips to Get Outta Town

by Kelsy Chauvin

EDGE Media Network Contributor

Friday August 21, 2020

Live Here? Go There: 5 Road Trips to Get Outta Town
  (Source:Galveston CVB)

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Summer 2020 is shaping up to be a road-trip kind of season. Across America, travelers are taking to the beaches, mountains, lakes, and forests to catch up on fresh air and nature. To help you refresh and decompress the gay way, we've compiled this tip sheet for your very own LGBTQ mini-break from five major U.S. cities. Gas up the car, pack up your travel cooler, and let's roll!


The drive from Houston to Galveston, Texas's go-to coastal resort town, is about an hour. (And about 3.5 hours from Austin.) That short jaunt leaves plenty of time to explore this quintessential beach city, home to a lively LGBTQ community.

Galveston hosts a rousing Pride celebration, this year slated for September 18 - 20. (Last year's Pride brought a brand-new rainbow crosswalk just outside City Hall.) There are more annual gay events, too, but no matter the season, LGBTQ travelers have plenty of choices for how to spend their time and money in this historic port city.

Much of the action is on the northern end of the island, around 25th Street. Robert's Lafitte is the self-proclaimed oldest gay bar in Texas (since 1970), hosting drag shows and other live events. A few blocks away, Rumors Beach Bar is perched on the along the beach, with wild nights of karaoke and drag bingo. Warm up your singing voice at 23rd Street Station Piano Bar, where Wednesday brings ladies' night.

For the freshest Gulf seafood and other local ingredients, don't miss Fish Company Taco, where Chef Daya Myers-Hurt serves up simple, affordable, delicious tacos and more. Gypsy Joynt is an eclectic, gay-friendly restaurant serving inventive comfort food and decadent desserts.

Get splashy with LGBTQ-owned Texas Scuba Adventures, which offers diving, charter boat trips, classes, and equipment rentals. If shopping is your bag, head to the charming downtown Postoffice District to browse wares by local artists at the gay-owned Old Galveston Trading Co. Or head to nearby Luna, an LGBTQ-owned home-décor boutique and gift shop.

(Source: Seven Hills Inn)

It's about 2.5 hours driving due west from Boston to reach the Berkshires, Western Massachusetts' section of the Green Mountains range. Once there, let the cool mountain breezes diffuse your stress and inspire loads of outdoor recreation.

The region makes a glorious escape for everything from hiking and golf to kayaking and horseback riding, not to mention camping, whitewater rafting and all manner of winter sports.

As an early leader in LGBTQ marriage equality and legal cannabis, Massachusetts is a famously progressive state, so queer travelers should find plenty of warm welcomes here. But for LGBTQ-owned businesses, dine at fun, fanciful Dream Away Lodge (actually a restaurant) in Becket. Or check into historic and queer-friendly. Or check into historic and queer-friendly, Seven Hills Inn in Lenox, set on 27 acres of lush lawns and stunning gardens.

Lenox also is home to lovely wine, beer, and pizza bar Brava. Don't miss a bit of shopping at gay-owned Casa B Group's, four Lenox clothing boutiques, including Casablanca, Shooz, and Swtrz. Just south of Lenox in Lee, find gay-friendly Moe's Tavern for craft beer and quality whiskeys — just don't ask for Coors Light.

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(Source: Out In the Vineyard)

From the gay Mecca of San Francisco, drive about 90 minutes north into Sonoma County for a gay old time in Guerneville. The Russian River hamlet is beloved by road trippers who discovered its cool, natural beauty decades ago. Guerneville remained just as charming as its early days, walking distance from the magnificent Armstrong Redwoods State Natural Reserve, and a scenic drive to the Pacific Coast.

In Guerneville, LGBTQ travelers have plenty of choices for dining, drinking, and lodging at gay-owned or -friendly establishments. On River Road, the main drag in town, dine at Big Bottom Market, bistro Boon Eat + Drink, and tequila bar Barrio. Friendly local watering hole Rainbow Cattle Company is there, too, as is gay-owned Equality Vines tasting room, which contributes to several LGBTQ organizations.

Flirtations and libations abound at the lively Main Bar at the R3 Hotel, which yes, is also a gay hotel. But gay-owned accommodations also await at boutique Boon Hotel + Spa, and rustic Johnson's Beach, an 11-acre vacation hideaway right on the Russian River.

Sonoma is one of the world's great wine-growing regions, so don't miss visits to tasting rooms around the county. About 25 minutes east in lovely Healdsburg, sample Bordeaux-style wines at the family-owned Aperture Cellars. Head southeast from Guerneville for spectacular sparkling wines at hilltop Iron Horse Vineyards, or join a casual outdoor tasting experience at biodynamic vineyard Porter-Bass.

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There's nothing like escaping the concrete jungle with an upstate getaway. Fortunately, the Hudson Valley is only about an hour or two north, with cute towns like Cold Spring, Beacon and Poughkeepsie dotting the eastern shore of the Hudson River; and New Paltz, Newburgh, and Kingston on the west side. Each offers artsy appeal and boasts lots of rainbow flags waving year-round, especially through summer Pride months.

Big Gay Hudson Valley is a good place to see what LGBTQ events are on the calendar, as is the Hudson Valley LGBTQ Community Center in Kingston. This summer will see most Hudson Valley Pride events held virtually, with hopes that in-person queer gatherings could still happen before fall.

Beacon is a favorite small town for its easy access, and scenic perch on the Hudson River. You can enjoy nature with hikes in Madam Brett Park, Mount Beacon, and Dennings Point State Park. Swing by Barb's Butchery on the way for a hearty sandwich, biscuits, or tacos to go.

This town is a hot spot for art lovers headed to the wonderful, Dia:Beacon (expected to reopen this summer). But strolling Main Street is a worthy diversion, with boutiques, antique shops and cafés along the way.

Grab a burger (meat- or plant-based) made with local ingredients and a well-made cocktail at Meyer's Olde Dutch Food & Such. Join a tasting or tour at Denning's Point Distillery, which produces a variety of small-batch, New York-inspired spirits. Further into town, you'll find Fishkill Creek at The Roundhouse, a hotel and refined restaurant overlooking the water, a perfect place to let nature (and wine) rush in.

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Key West, Florida
Key West, Florida  (Source: Getty Images)

It's a beautiful if lengthy, 3.5-hour ride from Miami to Key West. But once you're there, this southernmost American city will instill instant chill mode for your gay getaway. It's home to one of the most vibrant LGBTQ Pride celebrations each June. This year the affair has been moved to November 18-22.

Most queer nightlife is in the Pink Triangle area on Duval Street, Key West's main drag that's dotted with bars and clubs hosting loads drag. The hot spot is 801 Bourbon Bar, where the "801 Girls" take the stage for two shows nightly, plus bingo and karaoke nights. Aqua Bar and Night Club is another drag bonanza with nightly shows and dancing.

Enjoy fresh-caught seafood and boozy Sunday brunches at Blue Heaven in Bahama Village. For a breezy bite, hit Garbo's Grill, a festive taco truck with outdoor seating and a creative menu. Nearby is Caroline's Café, a casual eatery with great people-watching patios, serving some of the best local conch fritters (a Key West staple.)

Be sure to visit online or grab a copy of Q Magazine at LGBTQ bars and shops around town for upcoming events.

Click here for the latest COVID-19 travel recommendations and guidelines.

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Kelsy Chauvin is a writer, photographer and marketing consultant based in Brooklyn, New York. She specializes in travel, feature journalism, art, theater, architecture, construction and LGBTQ interests. Follow her on Instagram and Twitter at @kelsycc.