LGBTQ NYC: A 3-Day Itinerary

David Sokol

(Updated 10/10/2018)

A generation ago, LGBTQ+ visitors to New York City would have had to remain largely confined to the West Village to interact with their local community. But as social acceptance has gained and spread, so have the storefronts, restaurants and other businesses that are owned, operated and frequented by gays and lesbians. One great way to start your visit is with a pilgrimage to the famous crossroads of the West Village and Chelsea to soak in the history and local flavor of NYC’s LGBTQ+ culture. From there you can expand to Hell’s Kitchen and the newer, yet deeply rooted communities in northern Manhattan, Williamsburg and Queens.

Here’s a three-day route for eliciting the most meaning (and fun) from this mileage.

Day One: West Village and Chelsea

Today’s itinerary weaves through the sidewalks of both the West Village and Chelsea, so warm up for the healthy walk in Hudson River Park, a scenic and family-friendly replacement of the West Village’s piers that were synonymous with 1970s-era New York City gay life. After following in the footsteps of our predecessors, let your nose lead you back inland to Buvette Gastrothèque, on Grove Street. Breakfast at the cozy Jody Williams venture includes rustic bistro décor and a small, mouthwatering selection of crepes and tartines. If you’re looking for an early treat, stop by Big Gay Ice Cream, the fun and friendly LGBTQ+ owned soft serve spot with a unicorn painted on its window.

Continue heading east along Grove Street or the vibrant blocks of Christopher Street (the two merge) and you’ll end up at an intersection of Greenwich and Sixth Avenues: site of the Jefferson Market Library and its adjacent garden. This is a great area for shopping; across Sixth Avenue is C.O. Bigelow, an old-time apothecary where you can stock up on necessities, or head west up Greenwich Avenue to Jonathan Adler’s house of colorful ceramics, pillows and other whimsical products. Continuing along Greenwich Avenue, you can outfit yourself in high-end women’s clothes at Otte, athletic gear at Equinox and luggage of all sorts at Flight 001.

On Greenwich and Seventh Avenues, take a break in the new St. Vincent’s Triangle Park, which will be the future location of the New York City AIDS Memorial. This route also will take you past existing landmarks in gay history, including the 1964 O’Toole Building—originally designed by Albert Ledner for the National Maritime Union and later became part of St. Vincent’s Hospital, an early battleground in the AIDS crisis—as well as The Center, NYC’s vibrant LGBTQ+ community center that also has a coffee shop and a bookstore.

For lunch, head up to Chelsea where you can stop into the sleek local stalwart Cafeteria or the funky sandwich-and-salad café The Grey Dog. For shopping, don’t miss the Chelsea location of Housing Works Thrift Shop. With its stylish merchandise and inventive visual displays, this is a secondhand store par excellence. Sales help fund the services that Housing Works provides to homeless and low-income New Yorkers living with HIV/AIDS.

Consider returning to the West Village via The High Line. The elevated railway turned public park, designed by landscape architecture and urban design firm James Corner Field Operations with architects Diller Scofidio + Renfro, innovatively blends native plants and contemporary architecture with glimpses of the area’s industrial-era infrastructure. From Chelsea, you can take a downtown stroll on this green artery that will bring you to the Meatpacking District for more upscale shopping and people watching.

Back in the West Village, dedicate your evening to another good cause: culture. The Lucille Lortel Theatre—named for the woman who "put Off-Broadway on the map"—has been staging innovative theater since 1955. Another legendary, albeit more casual, venue is The Duplex. Whether you catch a cabaret show, queue up for open mic at the piano bar or just start a conversation with the servers, you’ll meet both established performers and young talents rising up the ranks. Afterward, check out a few more vaunted local haunts, namely Julius' and gay-rights cairn The Stonewall Inn for nightcaps; the blissfully decorated Cubbyhole and the subtler Henrietta Hudson serve a mixed but predominantly lesbian crowd.

Day Two: Hell's Kitchen and the Theatre District

While the West Village and Chelsea represent the historic LGBTQ+ landscape, the gay community is writing its next chapter in Hell’s Kitchen. Checking out this new center of activity demands a whole day’s attention, but it also wouldn’t be complete without taking in the Theatre District, which overlaps with HK and injects unique energy into the scene. Step one, then, is to buy tickets for any number of nearby Broadway shows that explore identity and self-expression, LGBTQ+ related or otherwise. Plan ahead here, or check theater box offices or the TKTS discount booth on the day of performance.

If you snapped up tickets for a matinee, take a quick walk to Vynl for lunch beforehand. This kitschy diner—which features a menu of comfort food mashed up with Thai favorites—is a longtime Hell’s Kitchen fixture. With the move came a slight dialing back of the B-52s-ish decor, but it’s still the most jubilant eatery in the neighborhood. And don’t miss the diva-themed restrooms!

Pre- or post-curtain, spend some quiet time at the Museum of Arts and Design, whose exhibitions of high-concept and meticulously crafted jewelry, furniture, fashion and objects celebrate the creative talent that often does not appear on stage or screen. MAD is located at the northeast corner of Hell’s Kitchen at 2 Columbus Circle; architecture aficionados will appreciate that the building was designed by Edward Durrell Stone in the 1960s and (not without controversy) reclad and renovated by Allied Works Architecture in 2008.

It’s back to Broadway (the world of it, not the actual street) for dinner. Barbetta is a Restaurant Row institution that has logged more than a century of service, and eating here feels like trespassing in a chateau’s drawing room. The wine list is as impressive as the atmosphere, and the food is delightful—though the courtyard dining area is even more so. While the stars shine brightly on Barbetta’s garden, for good food with a side dish of celebrity spotting, break bread instead at the almost-adjacent theater artist haven Joe Allen.

Finally, recap theater or menu highlights over drinks at Therapy. Inside this après-ski-style gay bar, there’s more talking than dancing among the crowd, which includes a sprinkling of women and professional men of all stripes. At rival Industry Bar next door, dancing is a more frequent occurrence; note the cash-only policy for drinks. Catch a drag show at either watering hole, or play the insider scouting the immense talents—drag queens among them—at a Feinstein’s/54 Below late show.

Day Three: Northern Manhattan, Williamsburg and Jackson Heights

Go out of bounds today, exploring the farther-flung places where gay life is staking a claim. Just remember that these emerging gayborhoods are primarily residential. Fewer LGBTQ+ visitors from elsewhere means fewer destinations that cater exclusively to the community, so you can mix up your itinerary with spots that appeal to everyone.

In northern Manhattan, where the LGBTQ+ population is highly visible in Hudson Heights and Inwood, that means spending the morning at the Met Cloisters. The museum, an assemblage of medieval-era buildings, houses approximately 2,000 works from the Metropolitan Museum of Art’s collection of medieval European art and architecture. The facility crowns a precipice of Fort Tryon Park, where you will also find an idyllic lunch destination in New Leaf. Besides alchemical cooking and an Ivy League setting, New Leaf boasts gay icon bona fides: the restaurant is operated by Bette Midler’s New York Restoration Project, and proceeds bolster NYRP’s support of Fort Tryon Park and many other green open spaces in New York.

Come early evening, act local and head from your park perch to Castro, an Inwood newcomer that has a multicultural discotheque vibe. Or think globally and make the trek to Jackson Heights. This Queens district is home to a large, mostly South American gay community, as well as a tremendous Indian population. In mainstay gay bar The Music Box, the melting pot just feels like a big dance party.

Brooklyn’s Williamsburg presents another option for your evening, though it probably deserves its own day of activity. Delight in the art of sustainable confection at Mast Brothers Chocolate, or remake yourself in the bearded image of the Mast Brothers themselves at Fellow Barber. For heartier nourishment, seek out the beloved Diner, later washing down the meal with brews from the very hip, slightly ironic gay bar Metropolitan. Want to make the day last even longer? Extend your stay at the boutique property Wythe Hotel. Designed to the last detail and run to anticipate your every need, the upscale crash pad will have hotel guests thinking they landed in a very cosmopolitan Oz.