Middleburg, Virginia, is a charming Southern destination known as the nation’s horse and hunt capital. Set against the backdrop of the Blue Ridge Mountains, Middleburg offers the best of small-town America: local art, historic landmarks, fine cuisine and one-of-a-kind boutiques. Middleburg is a place where you can enjoy world-class equestrian competitions, award-winning local wines and nationally recognized community events.
Middleburg was established in 1787 by American Revolutionary War Lieutenant Colonel and Virginia statesman John Leven Powell, who purchased the property from Joseph Chinn, a cousin of George Washington. Powell changed the name from “Chinn’s Crossroads” to Middleburg because the town was the halfway point between Alexandria and Winchester along the popular Ashby Gap trading route, along what is today Rte. 50.
Located in the heart of Virginia Hunt Country, the historic town of Upperville, Virginia offers the ideals of small town charm along the foothills of the Blue Ridge Mountains. Established in 1797 by Josephus Carr along the Alexandria-Winchester Turnpike, Upperville, Virginia today is regarded as one of America’s most revered equestrian communities. Despite its status as one of Virginia’s smallest town, Upperville, Virginia is the birthplace to many iconic Mid-Atlantic and Virginia Hunt Country traditions.
The Upperville Colt & Horse Show, established in 1853 by Richard Henry Dulany, represents the oldest continuously running horse show in the United States.
A designated landmark on the National Register of Historic places, Upperville, Virginia is also home to many of America’s most iconic country homes and estates, including Sandy Lerner’s Ayrshire Farm and Paul and Bunny’s Mellon’s Oak Spring Farm estate as well as a variety of charming 19th-century style brick, wood, and log homes along the upper-end of the town’s main thoroughfare.
Among its most notable architectural structures, Trinity Episcopal Church stands as one of the most significant in Upperville, Virginia. Designed by H. Page Cross in the French medieval parish style, it was donated by philanthropist Paul Mellon in the 1950s.
And for lovers of the outdoors and adventure, Sky Meadows State Park offers access to the Appalachian Trail and stunning vistas of the Blue Ridge Mountains across over 1,000 acres of protected park land.
Things to do in Middleburg and Upperville
Sky Meadows State Park
Hours: Wednesday-Sunday 10 a.m.-5 p.m.
Address: 11012 Edmonds Ln., Delaplane, VA 20144
National Sporting Library & Museum
Hours: Wednesday-Sunday 10 a.m.-5 p.m.
Address: 102 The Plains Rd., Middleburg, VA 20117
Boxwood Estate Winery
Hours: Thursday-Sunday 11 a.m.-6 p.m.
Address: 2042 Burrland Ln., Middleburg, VA 20117
Cana Vineyards and Winery of Middleburg
Hours: Saturday 11 a.m.-6 p.m.; Thursday, Friday, Sunday & Monday 12-6 p.m.
Address: 38600 John Mosby Highway, Middleburg, VA 20117
Greenhill Winery & Vineyards
Hours: Tasting Room open daily noon-sunset. Manor House (special events and Wine Club Members) open Friday-Sunday noon-sunset and Monday-Thursday by appointment only. Reservations can be made by visiting greenhillvineyards.com/reservations.
Address: 23595 Winery Ln., Middleburg, VA 20117
Red Fox Inn & Tavern
Hours: Monday-Friday 5-8 p.m., Saturday & Sunday 4:30-8 p.m.
Address: 2 E. Washington St., Middleburg, VA 20117
Salamander Resort & Spa
Salamander Resort & Spa is found in the charming and historic small town of Middleburg, Virginia, resting on 340 acres. The charismatic resort features 168 guestrooms and suites all with scenic views of the countryside. Truly dedicated to health and wellness, a 23,000-square-foot spa presents 14 treatment rooms and a private outdoor courtyard with heated pool. In addition, Salamander features 25 on-site acres dedicated to riding and a 14,000-square-foot stable. The culinary program also does not disappoint with the rustic Harrimans Virginia Piedmont Grill, a multi-experience cooking studio, well-appointed wine bar and jovial billiards room. Also offering zip lining, tennis, nature hikes, archery and an abundant amount of other outdoor activities, the adventures are endless.