17 Ways To Discover The Charm Of Williamsburg, Virginia

The colonial charmer is having a modern moment.

Williamsburg Inn
Photo: Photo: Peter Frank Edwards

When you chat with the locals in the town of Williamsburg, Virginia, you'll often hear the phrase "fall in love." Meandering through its 18th-century epicenter, it's easy to see why. Here, horse-drawn carriages clip-clop down cobbled streets lined with mature oaks; verdant fields are laid out like red carpets leading toward stately brick buildings; and white picket fences guard flurries of daffodils and flocks of sheep.

But the small-town charm extends far beyond its many colonial treasures. Today, Williamsburg's appeal lies in its ability to perform a delicate dance between old and new, between honoring its past and embracing a more modern future. Here are the top things to do to enjoy this charming town.

Experience Community

Brittany Rolston owns The Shoe Attic, a boutique in the heart of town. After living outside Washington, D.C., for years, Rolston says she's found something special in Williamsburg: community. "One of the biggest draws is the people," she says. "Everyone is so nice and welcoming, and I think that's what ultimately makes visitors fall in love with it and want to stay."

Colonial Williamsburg and Busch Gardens are popular attractions that Williamsburg has come to be known for, but there's more to explore. "Williamsburg has grown so much in the past few years," says Rolston. "People aren't coming here just for the history or theme parks anymore. They're coming to enjoy the town."

The Cheese Shop Williamsburg
Peter Frank Edwards

Browse the Shops

That sea change is evident in the bustling Merchants Square, where nearly 100-year-old general stores share sidewalks with contemporary boutiques and trendy taprooms. Those who know Williamsburg well find comfort in familiar mainstays like The Cheese Shop, a local institution famous for its stuffed sandwiches slathered in an addictive secret-recipe house dressing.

Retailers in Merchants Square range from the cute to the fabulously funky. For a whimsical mix of fashionable must-haves and statement-making wild cards, browse Rolston's The Shoe Attic. At French Twist Boutique find breezy closet staples (like the perfect linen dress) at reasonable prices. And if you're looking for something everyone can enjoy, The Peanut Shop of Williamsburg shows off famous Virginia peanuts in a plethora of flavors.

Get Outside

Be sure to take advantage of the network of rambling scenic trails. Ambitious runners and bikers can hit the winding, paved 52-mile Virginia Capital Trail, which travels through postcard-worthy pastures all the way from Jamestown to Richmond. Freedom Park offers shorter trails for hiking and biking with a side of history: It was once home to one of the earliest free Black settlements in America.

Grab a Bite

Serving elevated riffs on classic bar fare (like their delicious oak-smoked chicken wings), Amber Ox Public House has a rustic vibe and a roster of regulars (so be sure to make a reservation). Another gem of the city's food scene, Casa Pearl Oysters & Tacos—helmed by a young chef and veteran of Charleston, South Carolina's The Ordinary—delivers the Chesapeake Bay's finest bounty in a casual gas station turned oyster and taco bar.

Hit the Tasting Trail

The burgeoning Williamsburg Tasting Trail, which includes craft breweries, distilleries, wineries, and even a meadery (a marriage, once again, of past and present), is transforming the historic town into a boozy getaway. A few standouts: Billsburg Brewery serves up frosty pints in a peaceful marina-front setting. Silver Hand Meadery, meanwhile, reimagines the ancient sipper with rare and locally sourced varietal honey.

Resident Chris Smith along with business partner Robby Willey attended college here at William & Mary before setting off to pursue big-city career opportunities. But they both soon felt the familiar pull of small-town living and, putting their degrees in business and economics to use, decided to follow their dream of opening their own brewery. Williamsburg was the obvious choice. "It felt like a very authentic story—we met each other here, and we ultimately came back to a community that we wanted to support," says Smith.

Virginia Beer Co. Williamsburg
Photo: Peter Frank Edwards

After years of researching and planning, their The Virginia Beer Co. opened and is now among the slew of burgeoning businesses along the Williamsburg Tasting Trail. Housed in an old auto body shop—a cue taken from brew scenes in large cities—The Virginia Beer Co. is now a go-to spot on sunny Saturday afternoons when locals gather around communal picnic tables to clink frothy pints with names like Liquid Escape.

Amber Ox Williamsburg
Photo: Peter Frank Edwards

The Precarious Beer Project is luring city dwellers from Richmond and D.C. for a weekend (or even a lifetime). The 10,000-square-foot brewery and music venue and its Southern-style dining counterpart, Amber Ox Public House, which has its own Beer Lab, are also helmed by a pair of young investors, Chris Cook and Andrew Voss. But unlike many other local entrepreneurs who are inevitably lured back to Williamsburg, Voss (a Michigan native) had no previous connection to the town before he was wooed by an initial visit and decided to invest in it.

"What we've grown to appreciate about this place is that it feels very much like a small community, but it has this really cool downtown vibe," Voss says. "When people who don't know Williamsburg come to visit, they are often blown away by just how much there is to see and do here."

That's the magic of Williamsburg. Whether you come here for the unmatched historic character or craft brews, the friendly neighbors, or the bucolic beauty, it's a place that reels you in and keeps calling you back for more.

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