Twenty miles outside Charlottesville and about two hours from Washington, Gordonsville feels worlds away from the bustle of city life. Its downtown is just a couple of blocks long and features quaint shops that cater to the equestrians and gentleman farmers who live nearby.

“The traffic in Charlottesville is horrible,” says Barbara Drinkwater, a real-estate agent and longtime resident. “Here we call it the rush minute.”

Main Street had fallen into disrepair until a wealthy couple, Bruce and Jacqueline Gupton, bought many of the commercial buildings between 1998 and 2001 and, along with their son, Garrick, gave new life to the town. “If there had been an ‘ugly town’ award, it would have won,” says Bruce Gupton.

The Guptons’ efforts have attracted a Dutch spa, galleries, garden shops, a decorative blacksmith, and a high-end boutique. John Graves, who sells English art and antiques at his Old Somerset gallery on Main Street, likens the new atmosphere to that of a European-style High Street. “People from Georgetown and Richmond are coming here,” he says.

The centerpiece of the new Gordonsville is Pomme, a brasserie that has earned rave reviews. Chef Gerard Gasparini was working at an exclusive New Jersey country club when his business partner, Maurice Versailles, persuaded him to move. The pair recently opened the town’s newest attraction, a patisserie.

Gordonsville’s town-and-country atmosphere has prompted some to call it the next Middleburg, though Gordonsville is likely to remain far quieter. The Guptons have just two commercial buildings left to renovate and no plans to expand the business district.

That’s fine with locals such as Mayor Robert Coiner, who was born on Main Street. He praises the Guptons for preserving Gordonsville’s character.

“If Robert E. Lee and Stonewall Jackson were to walk down the street today,” Coiner says, “they would know exactly where they were.”

Once a railroad town, Gordonsville served as Jackson’s headquarters for several days in 1862. Later, the town’s Exchange Hotel became a Confederate hospital. (It’s now a Civil War museum.) James Madison’s Montpelier is less than ten miles away, and there are historic homes both in town and along scenic routes 20 and 231. Fox hunting, winetasting, and hiking the Blue Ridge Mountains are popular activities.

“We live in a picture postcard,” says Sharon Merrick, who owns S.H. Merrick Fashion & Interiors on Main Street and sells estate homes with her husband, Duke. Merrick says many Washingtonians are buying houses in and around Gordonsville to use as weekend getaways, with plans to retire here.

Proximity to Charlottesville, which is often named one of the country’s best places to live, is a big draw. The University of Virginia offers adult classes, cultural events, and top-notch medical care. When cravings strike, dragon rolls and veggie burritos are within driving distance.

Land is more readily available near Gordonsville than closer to Charlottesville, and prices are lower. In town, a three-bedroom bungalow renovated with “green” features recently listed for $285,000. A large historic home in excellent condition might fetch between $600,000 and $750,000, Merrick says, though none has come on the market lately.

Outside town, land typically costs $15,000 to $20,000 an acre. A farmhouse, horse stables, and pretty views will add to the price. For around $1 million, Merrick says, you could buy a renovated home with 10 to 20 acres.

Castle Hill—an 18th-century mansion with 600 acres of rolling countryside, two guest cottages, stables, and servants’ quarters—is available for $14.5 million.

The Guptons moved to Gordonsville in 1998 from the New York City suburb of Greenwich. “What attracted us to the area was Charlottesville,” says Bruce, whose company, Gupton Marrs International, consults for Fortune 100 companies. Then they discovered the ideal property, Rocklands, an estate with 2,200 acres.

The couple has come to love the town. “We go to Paris a lot,” says Bruce, whose wife is French. “The quality of life is no different.” When their Parisian friends ask about their hometown, Bruce tells them it’s “le plus beau village du monde”—the prettiest village in the world. 

More Up-and-Coming Towns

Berlin, a popular retirement destination on the Eastern Shore near Ocean City, aims to become an arts-and-entertainment center with galleries, restaurants, and cultural events. The movies Runaway Bride and Tuck Everlasting were filmed here.

Leonardtown is revitalizing its waterfront with a public park, dock, and townhouses. The College of Southern Maryland opened its St. Mary’s County branch here in the late 1990s, and there are plans for a winery cooperative.

Onancock’s new shops and restaurants have led some to call this Virginia Eastern Shore village on the bay the next St. Michaels.

Urbanna, on the Rappahannock River as it runs to the Chesapeake, has a new municipal marina, and a 700-home development is underway. It’s the home of Virginia’s official oyster festival.

This article is part of Washingtonian's Great Small Towns package. Click here to read about more great small towns.