This Small Town in Virginia’s Wine Country Has a 5-Star Hotel and Quaint Downtown—and It’s Just an Hour From D.C.

Upon entering Middleburg, Virginia (population 701), you’ll immediately get a sense of its equestrian heritage, deep appreciation of history, and enduring love of man’s best friend. The two-lane roads that feed into the town are lined with stone-walled farms and acres of rolling green pastures. As you meander through the bucolic landscape, keep an eye out for restored brick and fieldstone homes, horses, and the occasional winery. When you begin to see Federal-style townhouses, brick sidewalks, and a variety of dog-friendly antique stores, you’ll know you’ve arrived in Middleburg’s quaint historic district. 

Known as “the nation’s horse and hunt capital,” Middleburg is famously associated with steeplechasing and foxhunting; you may recognize the scarlet jackets, breeches, and black leather boots worn by the members of the Middleburg Hunt. What began as an English tradition is now firmly linked to Middleburg and Virginia Hunt Country, and visitors come from near and far to watch the mounted riders and foxhounds make their way down the main street during the holiday season (more on that later). 

Thanks to its proximity to Washington, D.C.—about an hour’s drive, barring rush-hour traffic—the small town has served as a luxurious countryside getaway for decades. “With its historic charm, boutique shops, and welcoming community, Middleburg is a welcome respite, especially if you live in a busy city,” says Wendy Osborn, owner of Chloe’s of Middleburg. And given its roster of award-winning hotels, wineries, and world-class restaurants, the town continues to attract travelers who want to experience the finer things in life, all while enjoying Virginia’s green spaces and fresh air. 

Interested in planning a trip to Middleburg? Read on to discover the best places to stay, eat, and explore.

Best Hotels & Resorts 

The Red Fox Inn & Tavern

The Red Fox Inn & Tavern is a stalwart character in Middleburg, with roots dating back to 1728. Spread out over five buildings, the property features 22 luxurious rooms, suites, and cottages. While its character may be defined by its history—ask the staff about its connections to Jackie O and George Washington—the inn embraces all of the modern comforts. Breakfast delivered to your door in a charming box? Just let the team know when you’d like it to arrive. 

Salamander Middleburg Resort & Spa 

A family-friendly resort set on 340 acres, Salamander Middleburg was opened in 2013 by Sheila Johnson, the co-founder of BET and America’s first Black female billionaire. “The grounds are gorgeous, with lots of on-site activities, and the rooms are beautiful,” says Mt. Defiance Cidery and Distillery’s manager, Nicole Nicastro, who also recommends a visit to the impressive 23,000-square-foot spa.

Goodstone Inn & Restaurant

Osborn calls the Goodstone Inn & Restaurant “the perfect choice for someone who is looking to stay in a more secluded property.” The inn’s six historic cottages and houses (with 18 rooms in total) are located just outside of downtown Middleburg. Spend your days biking, hiking, bird-watching, or lounging by the heated saltwater pool. To get the entire experience, be sure to dine at both on-site restaurants, The Bistro and The Conservatory.

Best Things to Do 

Explore Middleburg’s historic district.

To get the lay of the land, start your trip to Middleburg on foot. Over 160 of the town’s buildings are listed on the National Register of Historic Places—The Red Fox Inn & Tavern among them. “I always recommend strolling the main street… You can walk from one end of town to the other, without stopping, in 15 minutes, or easily spend two to three hours going into the boutiques, coffee shops, [and] antique stores,” says Elizabeth Gingerich, guest services supervisor at Salamander Middleburg. 

Visit the National Sporting Library and Museum and the Middleburg Museum. 

History is at the forefront of Middleburg’s narrative, so it should come as no surprise that there are a couple of places to learn about the area’s cultural heritage, traditions, and architecture. The National Sporting Library and Museum details “country pursuits,” including things like horsemanship, steeplechasing, foxhunting, and polo. While admission to the library is free, the museum does charge for entry. To get a deeper understanding of the history of the town itself, head to the Middleburg Museum.

Sip on Virginia wine, beer, cider, and spirits. 

While Loudoun County has been lauded as one of the top East Coast destinations for wine, the region can also claim several popular breweries, cideries, and distilleries. If you prefer reds and whites, head to Chrysalis Vineyards, Greenhill Vineyards, or Boxwood Winery, a historic landmark farm. Tastings are available at the Mt. Defiance Cider & Distillery, and beer drinkers can find their new favorite brew at nearby Lost Barrel Brewing. Parties without a designated driver can check out Expedition Vintage Tours, a service that takes you to and from local spots in a classic Land Rover. 

Attend the Middleburg Film Festival. 

The Middleburg Film Festival is an annual celebration of narrative and documentary films held in mid-October at the Salamander Middleburg Resort & Spa. Along with premieres and screenings, there are panels and conversations with filmmakers and actors. “Many of the featured films have gone on to win international awards,” says Osborn. The MFF was founded in 2013 by Sheila Johnson, who still serves on the board of directors. Tickets can be purchased online. 

Best Shopping

Middleburg Antique Gallery 

Part of the fun of visiting Middleburg is popping in and out of its many antique stores. “There are unique shops that you won’t find anywhere else with wonderful one-of-a-kind items,” says Nicastro. Take Middleburg Antique Gallery, for example. With 45 different dealers, the store offers an extensive selection of American and European furniture, rugs, books, chandeliers, fishing and sporting antiques, among other treasures. 

Highcliffe Clothiers

“Highcliffe Clothiers [has] modern British and Scottish attire and a little bit of equestrian wear thrown in,” says Gingerich. Self-described as an “old school haberdashery,” Highcliffe Clothiers offers custom clothing, plus ready-to-wear pieces and accessories. If you’re interested in going the custom route, be sure to request an appointment ahead of your visit. 

Crème de la Crème

“Crème de la Crème is a great shop to visit for French-inspired shopping,” says Nicastro. The inventory includes all sorts of home goods and gifts, like pottery, jewelry, linens, books, and the store’s signature candles. “It’s so fun to walk around and browse,” adds Gingerich. 

Chloe’s of Middleburg

Looking for a new vacation dress or a last-minute gift for a loved one? Stop in Chloe’s of Middleburg. Osborn fills her charming shop with bright colors, fun accessories, bath and body products, and specialty pet wear. 

Best Restaurants 

King Street Oyster Bar

“Great seafood, 10 different types of local oysters, nice outdoor seating, and happy hour every day” make King Street Oyster Bar one of the town’s best places to eat, according to Gingerich. The two-floor restaurant is centrally located on East Washington Street, and its drink menu includes seasonal cocktails, frosé, a house punch, and a house mule. 

Middleburg Common Grounds

For the “best coffee and breakfast sandwiches,” Gingerich recommends stopping at Middleburg Common Grounds. It’s the perfect grab-and-go spot if you’re gearing up for a hike in the surrounding area or have a full day of antiquing ahead of you.

The Upper Crust

“Owned by the Stine family, The Upper Crust is a favorite for baked goods that remind you of the way your grandma used to bake,” says Osborn. If you’re craving something sweet—think apple fritters, cinnamon buns, and croissants—you won’t leave disappointed. Not sure what to try first? “A local favorite is the cow puddle cookie,” Osborn adds. 

The Red Fox Inn & Tavern

As the name implies, The Red Fox Inn & Tavern is more than just a place to lay your head. The cozy, historic tavern, complete with working fireplaces, offers a delightful four-course dinner experience, best enjoyed with the Virginia and Tavern wine pairings. “The wonderful food is classic Virginia, and the cocktails are great,” says Nicastro. 

Middleburg Deli 

Sometimes something simple is the best choice, especially if we’re talking about lunch. Middleburg Deli, a tiny sandwich shop right off East Washington Street, has all of the staples, including hot dogs, Reubens, cheeseburgers, and good old-fashioned turkey sandwiches. Top it off with a bag of Route 11 chips and a brownie. 

Best Times to Visit 

The best time to visit Middleburg is from October through late December. “While all seasons in Middleburg are wonderful, the fall brings a particularly beautiful experience,” says Osborn. “The mild weather and vibrant foliage are not to be missed.” Check the calendar for a variety of equestrian events, including the International Gold Cup and the Virginia Fall Races, both of which occur in October.  

Middleburg also dresses to the nines for the holiday season, with festivities kicking off the first weekend of December during a multiday affair known as Christmas in Middleburg. “The whole town participates,” says Gingerich, who notes the highlights of the weekend are the two parades. The Middleburg Hunt, where mounted foxhunt riders and hounds make their way down the main street, precedes the Christmas Parade, a “traditional small-town parade ending with the arrival [of] Santa Claus,” she explains. 

How to Get There

Washington Dulles International Airport (IAD) is the closest airport to Middleburg. If you time it right and avoid rush-hour traffic, the drive should take around 35 minutes. Although farther away, Ronald Reagan Washington National Airport (DCA) is another option for travelers, with an average driving time of about an hour. 

How to Get Around

Downtown Middleburg is completely walkable, with sidewalks connecting the stores, restaurants, and shops. You will, however, need a car to explore the rest of Loudoun County and its many wineries, distilleries, and beautiful scenery.