The Ultimate Gay Road Trip

From rural West Virginia or South Carolina, to the rainbow-clad gayborhoods of Philadelphia and Louisville

June 6, 2025 11:00 am EDT
Connecting with community, far and wide.
Connecting with community, far and wide.
Getty Images

It turns out criss-crossing the country on a multi-state road trip in the midst of a heated election cycle was a rather surreal experience. Along with my husband, I took a huge leap this past summer into a life of semi-nomadism. We spiffed up our home in Oklahoma City to list on Airbnb, allowing us to travel more freely. Initially, we decided to take the scenic route to New England where I grew up, but we wound up extending our trip far longer than anticipated, taking us into another country and to numerous cities, towns, states and regions. And thus began what we dubbed our “Big Gay Road Trip,” seeking out queer culture along the way, be it an underrated gayborhood, an LGBTQ-owned inn or a queer-coded museum. 

Unintentionally, our road trip felt like a campaign blitz, but instead of wooing voters, we were doing something far more authentic: connecting with our community far and wide, in places new and old. Being recently back in O.K.C, incidentally right before the election, I look back on our Big Gay Road Trip with so much fondness and Pride, and most importantly, much hope for our great big complicated country. 

National Quilt Museum
The National Quilt Museum
Matt Kirouac-York

Quilts and Queens

Our first stop after leaving O.K.C (and ugly crying in our doorway) was Paducah, a small city on the western edge of Kentucky, where the Tennessee River meets the Ohio, and where the folk art scene is so rich that it earned elite distinction as one of only nine UNESCO Creative Cities in the U.S. Intrigued by its arts, and the fact that Paducah has held its own Pride festivals, it exemplified our quest for queer culture in unexpected places. And what could be unintentionally gayer than the National Quilt Museum? Along with a lineup of elaborate riverside murals, the museum helped earn Paducah its UNESCO designation, and rightfully so, considering the sheer array of bejeweled fiber art on display here, from a bedazzled saltwater crocodile to extremely detailed depictions of Lord of the Rings and Harry Potter

We stayed at the gay-owned 1857 Hotel, a lofty abode right in the historic riverfront district, and shopped for Pride merch at queer-friendly Bricolage Art Collective down the block. One night, while at The Cork Room wine bar for a nightcap, we couldn’t help but notice that almost everyone there was gay. “Just how gay is this little town?” we thought to ourselves, warmly. Turns out, we happened to be there during a recurring meet-up among local gays, so we fit right in. True to form, for a town of less than 30,000, Paducah is an apt reminder of the power of the arts, and how these expressive communities are often sanctuaries for queer residents and travelers alike, even in infamously red states. 

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From there, we went to a much bigger city that I had been to, yet one that still feels somehow underrated. Despite being one of the fastest-growing cities in the country, there’s something under-the-radar about my beloved Columbus, Ohio. It’s a city that feels at once metropolitan and homey, coupling that inherent Midwestern friendliness with big-city bravado — and all the queer-friendly amenities that come with it. Here, you’ll find one of the nation’s few remaining lesbian bars, Slammers, as well as quaint LGBTQ-owned restaurants, like convivial Barcelona, in equally quaint neighborhoods, like German Village. We visited Tremont Lounge, a relaxed, pub-like gay bar as old as I am, with friendly clientele and a mercifully low-volume playlist. One of my favorite neighborhoods is the Short North, a bustling district that really showcases Columbus’ metropolitan glow-up, with its myriad rooftop bars, boutique shops and, of course, the unabashedly gay mens’ store, Torso. Before we left, we hit up Parable Coffee, a Black- and queer-owned cafe and wine bar, with pastries, potables and vibes for days. And although we weren’t there in June, it’s worth noting that Columbus has a massive Pride festival (the biggest in the Midwest, after Chicago), which drew me to town for the first time in 2022. 

InnBuffalo
InnBuffalo
Matt Kirouac-York

Perhaps the most pleasant surprise on our Big Gay Road Trip was a city that neither of us had been to: Buffalo. Aptly nicknamed the Queen City, our gaydar drew us in and it impressed at every turn. Rust Belt cities, admittedly, are a blind spot for me, but there is absolutely nothing rusty about Buffalo — a city where well-preserved history stands proudly alongside splashy new developments (like the psychiatric hospital-turned-Richardson Hotel), envelope-pushing restaurants (like Southern Junction, where Texas-style barbecue meets Indian influence), and the coolest gayborhood I had never heard of, Allentown. We stayed at gay-owned InnBuffalo, a historic Victorian mansion in tree-lined Elmwood Village, which had big Agatha Christie murder mystery vibes (in the best way possible) and shopped for wine at lesbian-owned bottle shop Paradise Wine. While here, we learned about Buffalo’s history as a lesbian bar epicenter, best examined via the She Walked Here self-guided walking tour, which traces former watering holes like The 557 Club, Carousel, The Kitty Kat and Pink Pony. We also rented flamingo paddle boats at pastoral Hoyt Lake, in Frederick Law Olmsted-designed Delaware Park, which just felt inherently gay as hell. Around here, Niagara Falls tends to take most of the spotlight, and we obviously made a day trip there, the bucket list destination that it is, but don’t sleep on Buffalo. She’s a beauty. 

New Experiences in New England (and Beyond)

Once we made it to New England, it afforded me the first time to really explore my roots as an adult. Having left for college in Chicago, there is so much I never experienced there, including any of the region’s queer culture. 

Funnily enough, the city I grew up near in New Hampshire, Manchester, is also nicknamed Queen City. As a kid, I hated it. But that’s probably because high school is hard for closeted gay kids, and the only places I spent considerable time were the mall and the Barnes & Noble. Now, though, I was heartwarmed to watch a Hocus Pocus drag show at the Palace Theatre, a historic venue where I used to go on field trips (none of which included drag), followed by drinks at Manchester’s very own gay bar, The Stoned Wall Bar and Grill. Also, for the first time in nearly 20 years, I celebrated my birthday where I grew up, with my family. 

Downshift Coffee
Downshift Coffee
Matt Kirouac-York

In Maine, we bopped around Ogunquit, a town that my sister tipped me off as a particularly gay-friendly destination — and a fact quickly confirmed by its rainbow crosswalks, a gay section of Ogunquit Beach and a sprawling gay bar, Maine Street. Up the coast, we fell in love with towns like Belfast, which had numerous Pride flags at Downshift Coffee and inclusive bumper stickers — like “Say ‘I Do’ to Marriage Equality” — at The Green Store. We spent a couple days at Twin Ponds Lodge, a gay, clothing-optional campground in the rural town of Albion. The property was genuinely beautiful, with an outdoor pond for swimming and paddling, an indoor pool and hot tub, a stack of boardgames and hiking trails periodically decorated with sex swings. 

Vermont was the New England sleeper hit. We stayed at The Weston, a gorgeously rebranded boutique inn, with just five guest rooms and three suites, in a tiny town tucked in the Green Mountains. When we weren’t fumbling our way through games of croquet, or pairing wine with farm-fresh ratatouille at on-site brasserie The Left Bank, we were shopping for cute sundries nearby at The Vermont Country Store, a massive, rickety shop filled with vintage board games, flannel aplenty and enough maple syrup to satiate Buddy the Elf. We stopped in other cloyingly cute Vermont towns, like Brattleboro and Woodstock, before I took my husband to his first apple orchard, Scott Farm, where we shared cider donuts and I showed off my apple-juggling skills. 

Victoria-By-the-Sea
Victoria-by-the-Sea
Matt Kirouac-York

The furthest north we made it was Prince Edward Island in Canada — a place I used to visit every summer as a kid. My Nana’s homeland, it’s always been a special place for my family and me, and this was the first time I got to visit with my husband. Much like my home state, I wanted to explore queer culture in a place that was foundational to me, and much to my delight, there was plenty of it here, as seen in Victoria-by-the-Sea, an adorable seaside community that hosts its own Pride festival and teems with omnipresent Pride flags, billowing from vintage storefronts, old-timey chocolate shops and community playhouses. And at Green Gables Heritage Place in Cavendish, the setting that inspired L.M. Montgomery to pen her empowering — and possibly queer-coded — Anne of Green Gables novels. In front of the state-of-the-art museum, a Pride flag billows alongside a Canadian one, and inside, visitors can learn all about Anne’s close bond (which some have surmised was more than platonic) with her friend Diana. Notably, there’s a gay B&B on the island now, cheekily dubbed Green Gay Bulls B&B

My favorite part of that trip, though, was visiting Cows, an iconic local ice cream brand, known for its quirky cow-themed shirts, that I remember loving as a kid. This time, though, I strolled the rainbow crosswalk to the front door, hand-in-hand with my husband. Sure, they might not be serving full-blown Pride ice cream, but it was a clear link between my past and present, and one that showed the progress being made in places I’ve long felt connected to.  

Drag in Louisville
Drag in Louisville
Matt Kirouac-York

From Bourbon Country to the Lowcountry

After our stint in the Northeast, we embarked on the biggest whirlwind of the entire trip, through several states, multiple cities, and all manner of gay bars and businesses. 

First up was our trip to Kentucky’s inaugural Queer Bourbon Week, with stops throughout the state, including the Bardstown Road gayborhood in Louisville, the Gays & Dolls Prohibition Party in Covington and self-described “queer dive bar” Crossings in Lexington. While on a Pride-themed food tour in Louisville, our guide Hannah waxed poetic about their love for West Virginia’s mythical cryptid, Mothman. So, fittingly, on our way back to Pennsylvania, we veered off-course to visit the world’s only Mothman Museum in Point Pleasant, West Virginia, where the titular winged beast allegedly lurked for a couple years in the ‘60s. And while this may not seem like the gayest stop on our Big Gay Road Trip, we were tickled by the sassy, queer-coded Mothman signage inside, and by the weirdly sexy Mothman statue out front.

While Presidential campaigns were crawling all over Pennsylvania, we did the exact same, checking out Brownstone Lounge gay bar in Harrisburg (very chill!), and attending a happy hour in Hershey for Lambda, the largest LGBTQ+ car club on the continent, before making it to Philadelphia in time for the National Coming Out Day Parade. This was both of our first significant time in Philly, whose gayborhood had just been officially designated a historic neighborhood. Here, between all the rainbow crosswalks and gay bars, we meandered around Giovanni’s Room, the oldest LGBTQ+ bookstore in the country.  

Our next stop was our most anticipated: Washington, D.C. 

The author and his husband, Nathan, at Annie’s Paramount Steakhouse.
The author and his husband, Nathan, at Annie’s Paramount Steakhouse.
Matt Kirouac-York

I hadn’t been in years, and my husband hadn’t been since he was a kid, so neither of us had experienced any of the city’s queer culture — and as the U.S. city with the highest percentage of LGBTQ-identifying adults, there’s a ton of it here. Staying at the Dupont Circle Hotel, in the district long regarded as D.C.’s gayborhood, we were at once immersed in history, while experiencing a city actively reshaping the very structure of gayborhoods. As with some larger American cities, the concept has evolved and dispersed, growing from a smattering of gay bars in one area, to a city-wide landscape of inclusive spaces and businesses. Like Annie’s Paramount Steakhouse, an unabashedly campy eatery that’s been a pioneer for LGBTQ+ rights ever since its inception in 1948. Originally named Paramount Steak House, George Katinas renamed it after his sister, who fiercely advocated for the LGBTQ+ community, and was vocal about providing a safe space for her customers. Today, it’s the gayest steakhouse I’ve ever seen, with bracing Cosmos and a steady stream of regulars from all walks of life. D.C.’s restaurant scene is booming, and among the best in the nation at this point, but Annie’s was a dining experience I will remember most fondly. Especially for the fact that we met a friend from back home in O.K.C there for dinner. That, and our server had the excitable and theatrical energy of Little Orphan Annie, which I couldn’t tell was intentional or not, but I loved it either way. 

Some of our other favorite D.C. stops were Red Bear Brewing Co., the city’s only gay-owned brewpub, with beers like Dissent IPA and OktoBEARfest, and The Little Gay Pub, basically our dream gay bar, with chic decor, “Black Trans Lives Matter” signs and Silence of the Lambs and Casper playing behind the bar. 

Then it was finally back to the South. Growing up in New England, and living in Chicago for 13 years after that, I never expected to develop any kind of affinity for the South, let alone consider it more of a kindred home than anywhere. But there’s something about it: the pace of it, the food, the sunshine, the “y’all” of it all. It just feels right, even if many places in the South are not visibly as progressive or inclusive. But much like Oklahoma City, these are places filled with kind and welcoming people — folks who aren’t out to hate us, and are far more open-minded than they’re given credit for.

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Just take North Myrtle Beach. It’s not exactly a bastion of Pride, but I love it there. And not just because of its endless mini golf courses. Of all the places we stopped on our Big Gay Road Trip, this was probably the least gay, but it wound up being one of my favorite stops, for the genuine connections we were able to forge with locals. My husband and I learned the South Carolina state dance, the Shag, invented right here in North Myrtle Beach, from an older conservative couple who were nothing but kind and encouraging (and gracious about adjusting their pronouns throughout the heteronormative dance moves). The best, though, was when we were perched at Bar 19 Twelve, a swanky spot largely populated by conservative-looking locals. At one point, two older straight couples sat next to us at the bar, and gradually started making small talk. One woman, while talking about Key West, whispered “the homosexuals” to us, as if we’d be offended, and/or she’d be cancelled. “What do you like to be called?” she asked. Some people might retort, but it was clear that she was trying, and that she meant well. We conversed warmly and openly, and she offered to buy us drinks. And we just know that, after that, that group went home with a changed mindset about gay people. 

We spent the next week criss-crossing South Carolina, from seeing drag at Dudley’s in Charleston to designing my own flamingo hat at The Mercantile in Rock Hill and chatting with the gay couple who own Sterling Fox Antiques in Camden. It was so nice to be back in the South.

Dessert tasting menu in Atlanta.
Dessert tasting menu in Atlanta.
Matt Kirouac-York

Cornbread Madeleines, Funfetti Cookies and a Strip Club 

Our last leg took us through a few bigger cities, some of which were more obviously gay than others. 

Ironically, the gayest of them all — Atlanta — is where my husband and I went to our first strip club together. Ironic in the sense that it was a straight strip club, and a historic one at that. Clermont Lounge, Atlanta’s first and longest-running strip club, is still situated in the basement of the building that’s housed it since 1965. Said building has since been refurbished into the twee Hotel Clermont, with the addition of a snazzy French-accented brasserie and a bangin’ rooftop bar, but the strip club endures. And in true “gay men at a strip club” fashion, we preceded our experience with a dessert tasting menu at the hotel restaurant, courtesy of LGBTQ+ pastry chef Charmain Ware (with wine pairings by her wife), and brought our leftover cornbread madeleines into the club with us. Just in case we wanted a little snack later. 

In Nashville, things got even weirder, as our first stop was to the bakery owned by an ex-boyfriend. Pink Door Cookies is the colorful, whimsical brainchild of Mathew Rice, a pastry chef I met while living in Chicago some 13 or so years ago. In retrospect, we didn’t work as a couple, but one thing I’ve always known about him is how singularly talented he is. So when he moved to Nashville and started his own cookie brand during the pandemic, I couldn’t be more thrilled for him, and I couldn’t wait to make it to town so that I could introduce him to my husband and order one of everything. Just like the desserts I remember him making while we were dating, his cookies are distinctly nostalgic and playful, implementing fun frostings and rainbow sprinkles and “ingredients” like “Saturday Morning Vibes” for the Blueberry Pancake cookie, “Mom Frosting” with the Frosted Funfetti and “Unicorn Vibes” with the Cotton Candy. I think we’ll always have an awkward rapport nowadays, but I sure am happy for him, and even happier to support his endeavors.  

Elsewhere in Nashville, a city more typified by rambunctious bachelorette parties and heteronormative country bars, we had one of the best meals of the year at International Market. A full-circle experience for chef Arnold Myint, whose parents initially opened their own Thai-inspired International Market across the street in 1975, the restaurant serves the best Thai food I’ve had since literally being in Thailand. My husband, who is way pickier than he’ll ever admit to, can’t stop raving about it (and that Hatyai Thai fried chicken, specifically), months later. Even more endearing is that Myint is just as Proud as he is talented. He’s also the first chef I’ve met to moonlight as a drag queen, Suzy Wong. And in case that wasn’t enough fried chicken, I ordered something called “Glitter Chicken” at the Thompson Hotel bar where we were staying, and much to my delight, it was literally as advertised: a platter of chicken strips covered in edible glitter. 

“Glitter Chicken” at the Thompson Hotel bar
“Glitter Chicken” at the Thompson Hotel bar
Matt Kirouac-York

For one last stop before arriving back in O.K.C, we spent a couple nights in Memphis at The Memphian, a dazzlingly maximalist property in Overton Square, clad in all manner of animal prints, and complete with a rooftop bar — Tiger & Peacock — that has its own Caviar Concierge. Out front was a rainbow crosswalk, linking the boutique hotel with the rest of the Theater District, including the Playhouse on the Square and Lafayette’s Music Room. Inspired by all the animal print, we visited the Memphis Zoo, the coolest zoo I’ve seen since San Diego. It’s also the closest we’ve both ever been to a flock of flamingos, aptly dubbed a flamboyance. 

We made it back to O.K.C just in time to cast our early votes during the most tumultuous election of our lives. The results were not what we hoped for, but if there’s something that gave me solace, it was our experiences on this Big Gay Road Trip. Having newly traveled through such a wide swath of the country, both culturally and geographically, I knew that — despite what the election results suggested — a vast majority of Americans, on both sides of the political spectrum, are good. Most don’t want to fight; most want to meet us and connect with us, and just maybe, that connection will sway them at some point down their own road. It was also an important and empowering reminder that, as queer travelers, we belong wherever we want to be. We don’t need permission from Pride flags or rainbow crosswalks, nor the solidarity of a bustling city. As long as safety is top of mind, you belong anywhere your path may take you. 

For us, our trip was a timely reminder of all the beauty out there, from rural West Virginia or South Carolina, to the rainbow-clad gayborhoods of Philadelphia and Louisville, the campy steakhouses of D.C., the glittery cookies and chicken strips of Nashville, and all the queer heroes out there, continuing to pave the way.

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