For history lovers, there are few destinations in America as transporting as the living history museum known as Colonial Williamsburg, with its Dutch-Renaissance gardens and unmatched collections of English and American fine and decorative arts. There, actor-interpreters roam oak-shaded Duke of Gloucester (DoG) Street in full colonial garb, recalling America’s nascent Anglo-European history with a new, important emphasis on the lives and contributions of the city’s early Black population.
While Williamsburg, Virginia’s connection to history may be your first point of entry, there are new sites to love equally well, including the Virginia Capital Trail—51.7 paved miles open to cyclists, pedestrians, and adventurers, spanning from Williamsburg to Richmond. And then there’s the food: From biscuits to breweries, the city’s dining scene is worthy of a trip all its own.
Photo courtesy of the Virginia Trails Foundation
Where to Eat in Williamsburg
For a breakfast that sets the stage for a history-steeped day, the Old Chickahominy House is the clear choice. Often, biscuit makers go for height, stacking their layers to heaven, but Old Chickahominy is known instead for a flat, square biscuit that’s still fluffy but not so showy about it (and best enjoyed with the classic salty Virginia ham). And be sure to squirrel away a quart of Virginia’s beloved brunswick stew to enjoy back at the hotel.
Photo by Corey Miller
Since 1973, the Cheese Shop, a family-owned sandwich shop with a cut-to-order cheese counter, has been perfecting the art of unfussy sandwiches gilded with their craveable house dressing (now, thankfully available by the quart jar). Fill your picnic basket with sandwiches and selections from the well-appointed wine cellar downstairs before posting up on the patio overlooking bustling Merchants Square.
While exploring the Square, check out Precarious Beer Project, a casual beer hall and family-friendly spot to chill while having a go at half a dozen pinball machines, air hockey, and skeeball. Grab a pint and sample the sloppy-fun tacos and burritos from the Electric Circus walk-up taco bar on site
Whether on two wheels or two feet, discover the scenic pathways of the Virginia Capital Trail, where Spoke and Art Provisions is a welcome stop for giving your legs a rest while enjoying sandwiches or afternoon tea on Thursdays. Spoke and Art also offers rentable bikes and a bike-fixing station for all your cycling needs.
The patio at La Tienda, a paella and tapas bar, is the perfect place to relax after a day of trekking the trails or soaking up the history of DoG Street. Kick back with a carafe of sangria and impossibly thin and crispy fried eggplant with honey and thyme, and visit the market on the way out to stock up on tinned fish, fried tortas, and imported chorizo.
Photo courtesy of La Tienda
Dine from New School to Sichuan
When the dinner bell rings, head to the Cheese Shop’s sister restaurant, Fat Canary, helmed by chef Tom Power, where you’ll meander through a New American menu, starting with appetizers like the ginger barbecued pork ribs and crispy Rappahannock oysters, before cozying up to pan-seared sea scallops or free-range guinea fowl.
For a more international experience, you’ll find an outpost of James Beard award-winning chef Peter Chang’s Sichuan specialties—including the balloon-like scallion pancakes and duck in stone pot with mala, the sinus-clearing hot and numbing sauce—as well as Amiraj, an unlikely gem of inventive, modern Indian food with an award-winning wine list, nestled in an unassuming strip mall.
Don’t forget to load up on pies for the road at Jamestown Pie Company. Deep-dish varieties, like the au gratin pot pie with creamy shrimp, crabmeat, and scallops, are flaky nests for savory fillings. But the real stars are the sweet pies. Chocolate pecan is rich with a crunchy top—a contender in its class—and it doesn’t get any more local than the salty-sweet Virginia peanut pie.
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