Things to Do in Middleburg, VA
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.
The town has a rich history, including serving as the site of two skirmishes in 1863 as part of the Gettysburg Campaign during the Civil War. After the turn of the century, the town became a popular destination for foxhunting and steeplechasing, earning it a reputation as the “Nation’s Horse and Hunt Capital” and attracting well-known visitors from all over the country, including President John F. Kennedy.
With more than 160 buildings listed on the National Register of Historic Places, Middleburg is known for its natural beauty, historic charm, and Southern hospitality. Surrounding the town, you’ll find picturesque countryside, with low stone walls surrounding stately horse farms and cattle grazing in nearby fields–all with the Blue Ridge and Bull Run mountains as a scenic backdrop. With an ideal climate for growing grapes, Middleburg also boasts more than 20 wineries within 30 minutes of this historic hamlet, making it one of the top 10 wine destinations in the world.
Whether you’re looking for a historic tour, a scenic vineyard, a taste of the equestrian life or just a place to relax and have a good time, Middleburg has what you’re looking for. Please visit Middleburg’s visitor’s center at The Pink Box at 12 N. Madison St. or call 540-687-8888 (open daily from 11 a.m-3 p.m.) for more detailed information about the town’s offerings.
National Sporting Library & Museum
The National Sporting Library & Museum (NSLM) is located in the heart of beautiful hunt country. Founded in 1954, the renowned research library and fine art museum highlight the rich heritage and tradition of country pursuits. Angling, horsemanship, shooting, steeplechasing, foxhunting, flat racing, polo, coaching and wildlife are among the subjects one can explore in the organization’s general stacks, rare book holdings, archives and art collection. NSLM offers a wide variety of educational programs, exhibitions and family activities throughout the year and is open to researchers and the general public.
While there is no admission fee to the library, the museum charges $10 for adults and $8 for youths (age 13-18) and seniors. NSLM members and children age 12 and under are free.
Hours: Wednesday-Sunday 10 a.m.-5 p.m.
Address: 102 The Plains Rd., Middleburg, VA 20117
Boxwood Estate Winery
Boxwood Winery is located in an area steeped in Revolutionary, Civil War American history and renowned for world-famous horse farms. Today the area is also known as a wine region, Virginia being the fifth largest wine producing state. The Boxwood sustainable vineyards occupy 26.5 acres of the historic landmark farm and are planted with traditional Bordeaux varietals, predominately Cabernet Sauvignon, Merlot, Cabernet Franc and Sauvignon Blanc, all ENTAV certified by noted viticulturist Lucie Morton, who continues to consult on the vineyard.
Hours: Thursday-Sunday 11 a.m.-6 p.m.
Address: 2042 Burrland Ln., Middleburg, VA 20117
Cana Vineyards and Winery of Middleburg
Cana Vineyards and Winery is located in the beautiful Loudoun County countryside, nestled between the historic towns of Aldie and Middleburg on John Mosby Highway. Cana’s tasting room is situated on a picturesque hillside. The porch, patio and second-floor tasting room afford visitors a comfortable place to enjoy Cana wines while taking in the beauty of the surrounding Bull Run and Blue Ridge mountains.
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
Come experience 100% Virginia wine in an authentic Virginia wine and hunt country setting. As one of the foremost boutique destination wineries in Loudoun County, Greenhill delivers quality wine, with friendly and professional staff in a breathtaking Virginia wine country environment. Enjoy their wine, gather with friends and make new acquaintances in their authentic and earthy ambiance.
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
Middleburg Community Center
In the mid-1940’s, a group of civic-minded citizens came together to make Mrs. Howell E. Jackson’s dream come to fruition: to make Middleburg the social hub of Loudoun and Fauquier counties.
To this day, Middleburg Community Center’s mission has been to offer a gathering place for cultural, educational, and social activities to enrich the lives within our community.
As one of Loudoun County’s oldest nonprofits, MCC relies 100% on private donations to keep their doors open. MCC partners with over 70 local nonprofits and businesses to make all of their community events and programs possible.
Supported by the community for the community, the MCC is a place for private parties, weddings, corporate events & meetings, learning and child care, swim lessons, fitness classes, as well as a public outdoor space including an herb garden and patio, playgrounds, outdoor pool, ball field and picnic area. From small meetings upstairs to grand galas in the ballroom, the indoor facility can accommodate up to 400 people. The 5-acre property backs up with the Salamander Resort and includes a public pool, shaded picnic grounds, two playgrounds, open ﬁeld, and secluded herb garden and patio.
Over the years, the center has hosted the Kennedys, Liz Taylor, and Hank Williams, just to name a few. The citizens of Middleburg have fostered a pristine public space for everybody to enjoy.
Office Hours: Monday-Friday 9 a.m.-4 p.m.
Address: 300 W. Washington St., Middleburg, VA 20117
Red Fox Inn & Tavern
The Red Fox Inn & Tavern is a must-see Virginia landmark offering hearty meals in an historic tavern setting, romantic guest rooms fitted with traditional Piedmont furnishings, and unique weddings and social events that will create lasting memories for you and your guests.
Established in 1728, this historic fieldstone inn and tavern embodies the Piedmont’s cultural heritage and is inspired by four centuries of Virginia hunt country tradition.
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.
Hours: Open 24/7
Address: 500 N. Pendleton St., Middleburg, VA 20117
Discover a part of Northern Virginia’s industrial heritage — the restored gristmill at Aldie Mill Historic Park in Aldie. Built between 1807 and 1809, the Aldie Gristmill was once the largest factory of its kind in Loudoun County. The mill’s tandem metal waterwheels are fully operational, making it possible for visitors to watch live grinding demonstrations. Aldie Mill is available to rent for events and meetings. Tours and demonstrations are available during weekends between April and November.
Hours: Open for tours and grinding demonstrations April 9-Nov. 13 on Saturdays and Sundays from noon-5 p.m. Group tours can be accommodated on weekdays by appointment.
Address: 39401 John Mosby Hwy., Aldie, VA 20105