Visiting Virginia’s Horse Country

Middleburg commemorates 100 years of steeplechase racing.

The annual Middleburg Spring Races are held in April.

Photo courtesy of Middleburg Photo

This year marks the 100th running of a storied event that has taken place every April since 1921: the Middleburg Spring Races. Glenwood Park, five miles from Middleburg’s Washington Street, welcomes nationally ranked equestrians competing in a spectacle of pageantry and athleticism. Known for its natural beauty and ideal sporting features, Middleburg is considered the top equestrian and hunting center in the nation. “Our Middleburg Spring Races kick off the spring season,” says Middleburg’s mayor Bridge Littleton. “They are a bellwether event for the town, and we have thousands of people attending them. Nothing is as beautiful or well put together as Glenwood Park, and all profits go to the pediatric unit at INOVA Loudoun Hospital.” 

The hills and dales of Glenwood Park are the ancestral home of the annual steeplechase and embody the town’s commitment to protecting open spaces. Annie Bishop, a member of the races’ advisory board, has attended the event since she was a little girl. “The event has endured so long because the Middleburg community and surrounding area are steeped in horse tradition. People really want to protect that way of life and preserve the land for use of horses, steeplechase, and fox hunting. They’ve been good stewards of the land, helping to ensure that the tradition continues.” 

Julia Hanson, equestrian supervisor at Salamander Resort, with Patrick.

Photography by Jennifer Chase

Glenwood Park stands out for its undulating, impeccably groomed turf and the ability for spectators to view the entire racecourse while the horses are running. “You can see every single fence from wherever you are standing,” notes Bishop. “Glenwood Park is a beautiful venue. You’re looking at the Blue Ridge Mountains in the background, standing underneath oak trees that are 100 years old, beside old stone walls. Everything is starting to turn green. It’s magical.”

There are three types of contests at the Middleburg Spring Races: a flat race, timber races with fences made of wood, and hurdle races made of brush. But even those who aren’t particularly knowledgeable about steeplechase like to come for the tailgating. Bishop says attendees construct elaborate setups with floral arrangements, cocktails, and Champagne. They serve classic Southern dishes like fried chicken and deviled eggs. The race organizers invite Hammerdown Barbeque and Old Bust Head Brewing Co. to serve refreshments. Even youngsters get in the act by racing their stick ponies down the stretch. 

The love of horses is part of the town’s DNA, so Middleburg is the ideal home for the globally recognized National Sporting Library & Museum, a shrine to the niche topic of equestrian sports. “The Library has 4,000 rare books and 5,000 objects,” explains head librarian Michelle Guzman. “It’s a tiny subject, but people come from around the world to research equine and veterinary studies, hunting, and angling here.” In honor of 100th running, the museum will unveil Thrill of the ’Chace: Steeplechase in Art, a new exhibition showcasing paintings, sculptures, and works on paper from the National Sporting Library & Museum’s permanent collection and venues across the country.

Van Haute’s lightly cured king salmon appetizer is dotted with avocado and plated with pickled cucumber, buckwheat, and apple.

Observing majestic horses, visiting the museum, and shopping for bridles and breeches are just a few of the distinct experiences you can have in Middleburg. The town is likewise known for its hospitality. The Red Fox Inn & Tavern is the oldest continuously operating inn in America. The brick and stone buildings date back to the 18th century and served travelers on the wagon, and later, stagecoach trail. During the Civil War, The Red Fox Inn functioned as the meeting spot for Confederate cavalry commander John Mosby and his infamous Rangers. In the 20th century, President John F. Kennedy, who owned a home in Middleburg, held press conferences at the Red Fox Inn’s JEB Stuart Room. 

Chef Jan Van Haute at The Conservatory at Goodstone.

In contrast, the luxurious Salamander Resort & Spa is sparkling and modern, but inspired by the architectural traditions of Virginia’s countryside. The entrepreneur behind the resort is Sheila C. Johnson, founder of BET (Black Entertainment Television), a philanthropist, and the only African American woman to have ownership in three professional sports teams: the Washington Capitals, Washington Wizards, and Washington Mystics. Johnson is a longtime resident of Middleburg, and her daughter is an accomplished equestrian. When Johnson opened Salamander, the resort attracted new clientele seeking luxury accommodations, scenic recreation, and distinguished dining. 

Every space in the Salamander immerses guests in Middleburg’s proud heritage. A gifted artist, Johnson shot the landscape and nature photos in the guest rooms and installed horse-themed art throughout. Guests can participate in equine activities, such as group trail rides, on the 340-acre property, or enjoy cooking demonstrations, spa treatments, zip-lining, and children’s programs. The Salamander even offers art classes in which guests can create their own horse-inspired compositions. 

In Middleburg you can indulge your tastes in couture clothing and home décor or forage for antiques influenced by the horse and hound culture. Nearly all 40 retailers in Middleburg are independent shops. Don’t be surprised to meet a friendly storeowner like Wendy Osborn of Chloe’s, who graciously disperses fashion advice along with homespun health tips. 

Many of Middleburg’s food and beverage proprietors source ingredients from the plethora of nearby farms. Goodstone Inn & Restaurant, which sits on 265 acres of farmland, features seasonally driven meals in a three-story conservatory. Mt. Defiance Cidery & Distillery produces award-winning cider and spirits using Virginia-grown apples. 

Middleburg is also home to five wineries, many of which rely primarily on their own vineyards for fruit. At Greenhill Winery & Vineyards, general manager Jed Gray notes, “There’s a greater breadth of varietal wines here because our terroir is diverse.” Gray says visitors are captivated when they arrive. “They don’t expect to come out and see the landscape change so much; it feels so far away. Middleburg is a charming and architecturally beautiful town, with stone walls, country houses, mills, and farms. Drive down any road, and everyone has a name for their house, and they’re not just million-dollar abodes. It has changed but hasn’t changed at the same time.”

Mayor Bridge Littleton.

The Town of Middleburg has 700 residents who traditionally pick up their mail at the Middleburg Post Office, which informally functions like a town center, according to Mayor Littleton. Because Middleburg is such a coveted address, there’s always a waiting list. Surrounding the town are large estates owned by heirs and heiresses, including the Firestones and DuPonts, and celebrities like Robert Duvall. Elizabeth Taylor lived here when she was married to former U.S. Sen. John Warner.

Despite its reputation for understated glitz and glam, Middleburg is a soothing environment where you can relax and attend festive events. Some highlights include the Middleburg Film Festival, Historic Fall Festival, and Christmas in Middleburg, featuring a picture-perfect parade. In spring and summer, Middleburg hosts garden walks, ghost tours, and Sunday polo games. 

More than anything else, though, Middleburg has a small town feel, including the sociable merchants, an accessible main street (there’s no fee for parking), and the beautifully preserved countryside surrounding the town. Littleton says these features attract visitors time and again.

“When you come to Middleburg, you’re sure to make emotional connections. It’s our people; that’s what makes it so special,” says Littleton. “Besides being one of most beautiful parts of the state, you get to be a part of something that isn’t manufactured. Something that’s genuine.” So saddle up this spring, and visit the neighborly, picturesque town of Middleburg. 

The Red Fox Inn & Tavern.

Make It A Weekend

King Street Oyster Bar In addition to its signature oyster bar, this restaurant has the preeminent happy hour with a long list of $5 beverages and appetizers.

Middleburg Common Grounds The town’s favorite coffee and sandwich shop. The rustic bistro features counter service and showcases a gallery of local artists.

Goodstone Inn & Restaurant This exquisitely romantic inn serves farm-to-table French country cuisine. Chef Jan Van Haute, who formerly cooked for Belgium’s royal family, sources from Goodstone’s farm and vegetable garden, and the 1,500-bottle wine cellar features vintages from local vineyards. Ask about the monthly Farm & Vine Series.


Greenhill Winery & Vineyards The tasting room, clubhouse, and farm store create a wine tasting experience beloved by locals and luminaries alike.

Mt. Defiance Cidery & Distillery Located in downtown Middleburg and in a barn perched upon a sizable hill, this local beverage maker blends cutting-edge ciders and spirits.

Gold Cup Wine Bar Enjoy the height of sophisticated sipping at this clubby wine bar inside the Salamander Resort. Try Virginia wines, cocktails, and pub food with complimentary tastings on Sundays from 2 to 4 p.m.


National Sporting Library & Museum This unique complex celebrates the legacy of equine and angling sports with rotating exhibitions and an unparalleled collection of rare books and artifacts dedicated to the history of equine sports.

Aldie Mill Historic Park This restored gristmill, built in 1809, offers seasonal grain grinding demonstrations.

Sky Meadows State Park Twenty-two hiking trails with varying levels of difficulty offer access to the Appalachian Trail. Trails begin at the Historic Mt. Bleak-Skye Farm in Paris, circa 1780. From the ridge, take in vistas of farms, vineyards, and the peaks of the Shenandoah Mountains.

Pick Your Own Fruit Farms There are many market farms near Middleburg, like Crooked Run Orchard in Purcellville, which specializes in peaches, pears, sour cherries, and apples. At Wegmeyer Farms in Hamilton, you can harvest strawberries and heritage pumpkins.

Horseback Riding The equestrian center at Salamander Resort offers lessons in riding and grooming, as well as group and individual trail rides. At nearby Marriott Ranch in Hume, sign up for a public or private trail ride. Both centers welcome riders of all levels.

Greenhill Winery & Vineyards.

Where to Stay: 

Salamander Resort & Spa Elegant Forbes five-star hotel with a host of amenities, luxurious guest rooms, and a world-class spa.

Briar Patch Bed & Breakfast Inn Country hospitality with stunning mountain views, evening barbecues, and cooking classes.

Goodstone Inn & Restaurant Five-star guest rooms and cottages on expansive farmland. Amenities include a pool terrace, trails for hiking and biking, and canoeing on Goose Creek. The larger cottages are perfect for groups and families.

The Inn at Evergreen Modern, upscale inn on a former plantation property, featuring golf, swimming, and tennis.

The 100th Middleburg Spring Races have been rescheduled to June 13, 2020. Unfortunately, due to the COVID-19 pandemic, the races will not be open to the public. Please visit for details. This article originally appeared in our April 2020 issue.

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