Ultimate Guide to Planning Your Middleburg, Virginia Getaway

Upon entering Middleburg, Virginia (population 663), you’ll immediately sense its rich equestrian heritage and deep appreciation of history. The scenic two-lane roads leading into town are often lined with charming stone-walled farms and rolling green pastures. As you wander through this picturesque landscape, you may encounter restored brick and fieldstone homes, horses grazing, and the occasional winery. When Federal-style townhouses and diverse, dog-friendly antique stores come into view, you’ll know you’ve arrived in the quaint historic district of Middleburg.

Nicknamed “the horse and hunt capital of the nation,” Middleburg is widely recognized for its steeplechasing and foxhunting traditions. Visitors may spot the elegant scarlet jackets and black leather boots worn by the members of the Middleburg Hunt. What began as an English tradition is now intricately woven into the fabric of Middleburg and Virginia Hunt Country. During the holiday season, spectators flock to observe the impressive mounted riders and foxhounds parade down the main street.

Thanks to its close proximity to Washington, D.C., only about an hour’s drive away (traffic permitting), Middleburg has been a luxurious countryside retreat for generations. “With its historic charm, boutique shops, and friendly community, Middleburg offers a welcome respite, especially for urban dwellers,” explains Wendy Osborn, owner of Chloe’s of Middleburg. The town is renowned for its award-winning hotels, wineries, and world-class dining options, drawing travelers eager to indulge in the finer things in life while basking in Virginia’s natural beauty.

Read on to discover the best places to stay, eat, and explore in the enchanting town of Middleburg.

Best Hotels and Resorts in Middleburg

The Red Fox Inn & Tavern

The Red Fox Inn & Tavern boasts a storied history, dating back to 1728. Nestled across five buildings, the inn offers 22 luxurious rooms, suites, and cottages. While it exudes historical charm—ask the staff about connections to Jackie O and George Washington—it also encompasses modern comforts. A delightful breakfast served in your room? Just inform the team of your preferred delivery time.

Salamander Middleburg Resort & Spa

Renowned as one of the best hotel brands, Salamander Middleburg is situated on the edge of downtown. Opened in 2013 by Sheila Johnson—the co-founder of BET—this family-friendly resort spans 340 acres. “The grounds are stunning, featuring numerous onsite activities, and the rooms are exquisite,” remarks Nicole Nicastro, manager of Mt. Defiance Cidery and Distillery, who also recommends a visit to the grand 23,000-square-foot spa.

Goodstone Inn & Restaurant

Osborn describes Goodstone Inn & Restaurant as an “ideal choice for guests seeking a more secluded property.” Located just outside of downtown Middleburg, Goodstone features six historic cottages and houses, accommodating a total of 18 rooms. Guests can enjoy biking, hiking, birdwatching, or unwind by the heated saltwater pool. To complete your stay, don’t miss dining at The Bistro at Goodstone and The Conservatory at Goodstone.

Best Things to Do in Middleburg

Explore Middleburg’s Historic District

For a comprehensive understanding of Middleburg, begin your visit on foot. Over 160 buildings in the town are listed on the National Register of Historic Places, including The Red Fox Inn & Tavern. “Walking the main street is highly recommended; it takes just 15 minutes to stroll from one end to the other, or you can easily spend two to three hours exploring the boutiques, coffee shops, and antique stores,” advises Elizabeth Gingerich, guest services supervisor at Salamander Middleburg.

Visit the National Sporting Library and Museum and the Middleburg Museum

The National Sporting Library and Museum honors “country pursuits”—including activities like horsemanship, steeplechasing, foxhunting, and polo. Admission to the library is complimentary, while there is a fee for museum entry. To gain deeper insights into the town’s history, visiting the Middleburg Museum is well worth your time.

Sip on Virginia Wine, Beer, Cider, and Spirits

Loudoun County is celebrated as a premier East Coast wine destination, also home to several breweries, cideries, and distilleries. For wine enthusiasts, explore Chrysalis Vineyards, Greenhill Vineyards, or Boxwood Winery, a historic landmark. Cider tastings can be enjoyed at the Mt. Defiance Cider Barn, while craft beer aficionados can sample new favorites at Lost Barrel Brewing. For those without a designated driver, consider booking a tour with Expedition Vintage Tours, providing safe transportation to 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 every fall at the Salamander Middleburg Resort & Spa. Featuring premieres, screenings, and engaging panels with filmmakers, it’s a cultural highlight. “Many featured films have garnered international awards,” says Osborn. Now in its 11th year, the festival, founded by Sheila Johnson, offers tickets that are available online.

Best Shopping in Middleburg

Middleburg Antique Gallery

Exploring Middleburg’s antique stores is a delightful experience. “Unique shops offer one-of-a-kind items that you won’t find anywhere else,” notes Nicastro. For instance, Middleburg Antique Gallery features over 45 dealers showcasing a vast selection of American and European furniture, rugs, chandeliers, and sporting antiques.

Highcliffe Clothiers

Highcliffe Clothiers specializes in modern British and Scottish attire with an equestrian twist. This “old school haberdashery” provides custom clothing and ready-to-wear pieces. Be sure to schedule an appointment if you wish to explore custom options.

Crème de la Crème

If you’re after French-inspired treasures, Crème de la Crème is a must-visit. The store offers an array of home goods, gifts, pottery, jewelry, and their signature candles—perfect for browsing. “It’s so enjoyable to explore,” adds Gingerich.

Chloe’s of Middleburg

For vacation wear or last-minute gifts, visit Chloe’s of Middleburg. Osborn began her vibrant shop in 2019, filled with colorful attire, appealing accessories, bath and body products, and specialty pet accessories.

Best Restaurants in Middleburg

King Street Oyster Bar

Renowned for its “great seafood, 10 local oyster varieties, delightful outdoor seating, and daily happy hour,” King Street Oyster Bar is among the finest dining experiences in Middleburg. Located on East Washington Street, the two-story restaurant features seasonal cocktails, frosé, and house specialties.

Middleburg Common Grounds

Gingerich recommends Middleburg Common Grounds for “the best coffee and breakfast sandwiches.” It’s an ideal spot for a quick breakfast before a day of hiking or shopping.

The Upper Crust

Family-owned and cherished, The Upper Crust is famous for baked goods that evoke nostalgia. From apple fritters to croissants, the sweet treats are a must-try. “A favorite among locals is the cow puddle cookie,” adds Osborn.

The Red Fox Inn & Tavern

The Red Fox Inn & Tavern offers more than just accommodations; it features a cozy historical tavern with working fireplaces. Here, guests can savor a delightful four-course dinner, ideally paired with Virginia wines. “The food is classic Virginia, and the cocktails are fantastic,” remarks Nicastro.

Middleburg Deli

For lunch, simplicity reigns supreme at Middleburg Deli. Conveniently located off East Washington Street, it offers all the sandwich staples, including hot dogs, Reubens, and turkey sandwiches topped off with Route 11 chips and a brownie.

Best Times to Visit Middleburg

The most opportune time to visit Middleburg is from October to late December. “While every season is delightful, fall offers an especially picturesque experience,” notes Osborn, highlighting the mild weather and vibrant foliage. Check local calendars for various equestrian events like the International Gold Cup and the Virginia Fall Races, both held in October.

In anticipation of the holiday season, Middleburg transforms into a festive wonderland starting the first weekend of December, marked by the Christmas in Middleburg celebration. “The entire town gets involved,” recounts Gingerich, who’s excited about the dual parades featuring the Middleburg Hunt and Hounds Review followed by the traditional Christmas parade, culminating in the arrival of Santa Claus.

How to Get There

Washington Dulles International Airport (IAD) is the nearest airport to Middleburg. If you time your journey right—avoiding rush-hour traffic—the drive takes around 35 minutes. Ronald Reagan Washington National Airport (DCA), although further away, is another viable option, taking approximately an hour.

How to Get Around

Getting around downtown Middleburg is easy and pedestrian-friendly, with sidewalks connecting shops, restaurants, and attractions. However, to explore the wider Loudoun County and its renowned wineries and distilleries, a car is necessary.