Discover the Charm of Williamsburg, Virginia, The South's Best Small Town 2020
The colonial charmer is having a modern moment.
Like many others who pass through Williamsburg, Virginia, Brittany Rolston has fond memories of the historic town that can be summed up in a single faded snapshot: “I was 4 years old sitting on a cannon in front of the Governor’s Palace. I knew this town for Colonial Williamsburg and Busch Gardens, and that was about it.”
Three decades later, she sees this southeastern Virginia spot much differently. At 35, the Williamsburg local owns a boutique, The Shoe Attic, in the heart of town and can walk there from her home. She has a hard time telling you where her favorite places to eat and drink are because there are way too many to choose from. 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.”
When you chat with the locals in town, 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, the appeal lies in its ability to perform a delicate dance between old and new, between honoring its past and embracing a more modern future. “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.”
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. Others are discovering the city’s magic for the first time, with spots like the Precarious Beer Project, a 10,000-square-foot brewery and music venue, luring city dwellers from Richmond and D.C. for a weekend (or even a lifetime).
Then there are those, like resident Chris Smith, who are rediscovering— and investing in—Williamsburg in the midst of its renaissance. Along with business partner Robby Willey, Smith 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.
After four years of researching and planning, The Virginia Beer Co. opened and is now among the slew of burgeoning businesses along the Williamsburg Tasting Trail, which includes craft breweries, distilleries, wineries, and even a meadery (a marriage, once again, of past and present). Housed in an old auto body shop—a cue taken from brew scenes in large cities— it’s 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.
The same goes for Precarious Beer Project and its Southern-style dining counterpart, Amber Ox Public House, which has its own Beer Lab. Amber Ox is 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 decided to invest in it. Wooed by an initial visit, he uprooted his family despite having a fresh mortgage and says, “We haven’t second-guessed it for a minute.”
“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 bucolic beauty, it’s a place that reels you in and keeps calling you back for more.
WATCH: 2020 South's Best Small Towns
Enjoy Williamsburg Like a Local
EAT: Serving elevated riffs on classic bar fare (like their delicious oak-smoked fried chicken wings), Amber Ox has a rustic vibe and a roster of regulars (so be sure to make a reservation). Another newbie to the 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.
DRINK: The burgeoning Williamsburg Tasting Trail 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.
DO: 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.
SHOP: 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 The Shoe Attic. Quirks is a favorite among locals for lots of creative gift ideas, and French Twist Boutique offers breezy closet staples (like the perfect linen dress) at reasonable prices.