A familiar tourist destination, Virginia often gets skipped over by travelers looking to shake things up. But the Old Dominion is worthy of a road trip unto itself — looping through the state feels like visiting a microcosm of the U.S., with cultural touch points from every corner of the county compressed into one scenic and historic tract of land.
Start: Washington, D.C. End: Washington, D.C.
Total Distance: 475 Miles. Suggested Length: 5 to 7 days.
1) Skyline Drive
Shenandoah National Park
Shenandoah’s singular ribbon of gray road, Skyline Drive, ambles through every green corner of the preserve as it follows the crest of the Blue Ridge Mountains. The hundred-plus miles of track promise 69 stop-worthy lookout points over dozens of tree-filled valleys and cool lakelets.
While most of Richmond looks like it’s right out of Midnight in the Garden of Good and Evil, the Carytown district is awash in psychedelic colors. Wander down the main commercial drag, Cary Street, to find gay-owned gift and home goods store Mongrel, where everything is so perfectly displayed you’ll end up walking out with a dozen items. If your eyes need a break from the acid trip of funky facades, stop by the nearby brand-new Institute for Contemporary Art, a starkly minimalist expression of sculpture-architecture designed by Steven Holl.
3) Roaring Pines
The promising Roaring Pines is an outpost on the edge of the newly revitalizing Church Hill neighborhood. It’s a soda fountain parlor selling curative drinking vinegars alongside American-made home essentials, and one of the first signs that Richmond is poised to become the Portland of the South. Afterward, pop into Sub Rosa up the street for the best pastries and cakes in town.
Dinnertime at gay-owned L’Opossum is like visiting Liberace’s garage sale, festooned with embroidered erotica and suggestive stained glass. Southern-style mains are approached with the discipline of a French kitchen. And don’t forget about dessert, with not-so-coyly named sweets like the “Hot Black Bottom” and the “Swashbuckling Bundt Pirate.”
5) Merroir: A Tasting Room
If you’re a fan of Rappahannock in downtown Richmond (or the more relaxed Rapp Session next door) then make the journey out to coastal Virginia for oysters plucked straight from the source. Right on the namesake Rappahannock River, Merroir brings bivalves to the table raw, or cooks them on an open grill.
6) Pope-Leighey House
The Pope-Leighey House draws much of its inspiration from Frank Lloyd Wright’s time in Japan. An ingenious floor plan and animalistic wall carvings let in ample light that dances along the home’s wooden paneling throughout the day. Although it’s only around 1,200 square feet, it’s easy to spend several hours inside admiring the attention to detail and the masterful design of its modular furniture.
7) Torpedo Factory Art Center
Once a munitions plant that also stored sensitive government documents and dinosaur bones after WWII, the Torpedo Factory became a haven for pot-smoking teens with spray cans in the ’60s until it was purchased by the municipal government and transformed into artist workshops a decade later. Today, more than 80 ateliers thrive in the airy, interactive space. Visit Lisa Schumaier, a native Alexandrian who makes whimsical ceramic sculptures and relief paintings from unexpected items like used chewing gum. Upstairs, Marcel Artes Deolazo works super-gay erotica into all of his media, from Christmas ornaments to postcards.
8) King Street
The main artery in downtown Alexandria bears all the charm of a Nancy Meyers Christmas flick, and then some. Don’t miss the Stabler-Leadbeater Apothecary Museum, a pharmacy preserved from the 1800s containing potions in dusky beakers and parchment prescriptions in towering wooden cabinets. Down the street, The Hour is a stunningly curated boutique dedicated to the lost art of the cocktail, vending hundreds of stemware selections and bar cart accoutrements. Carbo-load at LGBTQ-owned Hank’s Pasta Bar, which hosts a monthly drag brunch, then toast your trip at the super-secret Captain Gregory’s, a cocktail lounge and dessert parlor hidden behind a trick wall in a Sugar Shack Donuts.