Overview
Middleburg is a town of 800 people (2019) in Virginia known as the capital of horse country. This quaint town features historic architecture, tree-lined streets, charming and unique shops, and a variety of dining establishments. Middleburg is also home to The Red Fox Inn, touted as the oldest original inn in the country.
Middleburg is a popular place for celebrities to reside or start a second home. Local celebrity residents include Robert Duvall and Willard Scott. Past residents have included President John F. Kennedy and Jackie Kennedy, Elizabeth Taylor, and Pamela Harriman. Olympic equestrian riders, Fortune 500, and heirs are included in the towns prestigious list of residents.
The Civil War features prominently in the town's history, as troops from both Union and Confederate armies camped and skirmished here on their way to Gettysburg. Confederate Colonel John S. Mosby used Middleburg as a base camp from which to raid nearby Union outposts. Self-guided driving tour brochures, audio tapes, and CDs on the Mosby Heritage Area are available for purchase at the Loudoun County Visitors Center in Leesburg.
Annual Middleburg events include the Hunt County Stable Tour held on Memorial Day weekend when more than a dozen major horse estates and equine facilities open their doors to the public, and the annual Christmas Parade on the first Saturday in December which is led by the hounds of the local hunt followed by riders on horseback in their traditional hunting attire.
6 sights · 1 things to do · 10 places to eat · 3 bars & cafés · 3 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Middleburg
The National Sporting Library
A research center that preserves and shares the art, literature, and culture of horse and field sports. Rotating exhibits.
Fox Chase Farm
Equestrian and event facility located on Route 50. Hosts horse shows for many disciplines, as well as bus tours, riding demonstrations, pony parties for birthdays, farm-to-table dinners and other events.
Greenhill Winery & Vineyards
11 acres of vineyards set against the Blue Ridge Mountain range.
Middleburg Community Center
Community center featuring public outdoor space including an herb garden and patio, playgrounds, outdoor pool, ball field and picnic area.
The Pink Box
Middleburg's visitors' center.
Red Fox Inn & Tavern
Listed on the National Register of Historic Places, still operational as a Drink/Eat/Sleep option, the Red Fox Inn is one of the oldest continuously operated inns in the United States.
Plan your trip
Best time to visit & weather
Most comfortable: Apr–Oct. Summer highs reach about 90°F; winter lows dip to about 30°F. Very hot (Jul) — plan outdoor time for mornings. Wettest: Jul and Jun. (climate data from nearby Washington, D.C.)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- IAD Washington Dulles International Airport, Dulles — 15 mi away (major hub). Directions
- DCA Ronald Reagan Washington National Airport, Washington — 38 mi away (major hub). Directions
Getting to Middleburg requires a car, and it is on US-50. Coming from D.C., it is best to pick up US-50 from I-66 W. Once you are here, the village is delightfully walkable.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 2-day itinerary
Day 1
- Morning The National Sporting Library, Greenhill Winery & Vineyards
- Lunch Red Fox Inn and Tavern
- Afternoon The Pink Box, Empower Adventure Middleburg LLC
- Dinner The French Hound
- Evening Mount Defiance Cidery and Distillery
Day 2
- Morning Middleburg Community Center, Fox Chase Farm
- Lunch Market Salamander
- Afternoon Red Fox Inn & Tavern
- Dinner Goodstone Inn and Restaurant
- Evening Gold Cup Wine Bar
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Map
Every listing with a location. Tap a pin for its Google Maps link.
Get in
Getting to Middleburg requires a car, and it is on US-50. Coming from D.C., it is best to pick up US-50 from I-66 W. Once you are here, the village is delightfully walkable.
See
Buy
Shop Journeymen Saddlers
Casual country clothing for men and women. Gifts, accessories and repairs.
Shop Foxfire Antiquities & Objets D'Art
Shop The Outpost
Retail shop specializing in authentic British campaign antiques, sporting and club antiques, vintage textiles and rugs, and unique finds from around the globe.
Shop The Shaggy Ram
Shop Second Chapter Books
Independent bookstore with new and used books, newspapers, handmade greeting cards, reading games and skill development items, meeting/reading space, free wifi and coffee.
Shop The Tack Box Inc.
Offers tack and equestrian attire for many disciplines such as eventing, fox hunting, racing and showing for the professional to the pleasure rider, along with accessories and supplies for the stable. Also provides services including boot and saddle fittings, custom equestrian linens, tack drapes, custom trunks, nameplates, clipper and blade service, blanket cleaning and repair, horse vacuum service and repair, and tack oiling.
Shop Thomas Hays & Son Jewelers
Offers antique and contemporary jewelry and silver. Fine custom jewelry and repair.
Shop Tully Rector
Women’s contemporary clothing and accessories. Beauty boutique, skincare, make-up, all else beauty.
Eat
Eat The French Hound
French inspired bistro.
Eat Market Salamander
Working chefs market with prepared foods, wine, cheese & other gourmet food products.
Eat Goodstone Inn and Restaurant
Farm-to-table gourmet dining. Executive Chef William Walden brings years of experience and expertise in creating French cuisine keeping to traditional and classical preparations.
Eat Harrimans Virginia Piedmont Grill
Features fresh, seasonal ingredients, from the Chef’s garden just outside the restaurant.
Eat Home Farm Store
Home Farm is Ayrshire Farm’s butcher shop and grocery store featuring U.S. and Virginia sourced products. The beef, pork, veal, chicken and turkey products are all Certified Humane and Certified Organic.
Eat Market Salamander
Offers a café with gourmet sandwiches to go.
Eat Middleburg Common Grounds
A local favorite — coffee, tea, beer, wine — breakfast sandwiches all day — salads — soup — sandwiches — local providers whenever possible — rotating art gallery of local artists.
Eat Popcorn Monkey
Family-owned gourmet popcorn shop specializing in handmade, fresh popcorn in small batches. Sports popcorn tins, cinnamon glazed nuts, retro candy and more.
Eat Red Fox Inn and Tavern
Lovely American restaurant featuring good quality meals in a comfortable setting. Hearty breakfasts, casual lunches and elegant candlelight dinners await you in the Red Fox Inn's cozy dining rooms which display original stone fireplaces and hand-hewn ceiling beams over thick fieldstone walls. The seasonal menus feature many local ingredients sourced from farms in the area. The Inn's wine list includes a vast selection of domestic and imported vintages and showcases many wines from local vineyards.
Drink
Drink Gold Cup Wine Bar
Piedmont-inspired cuisine paired with featured Virginia and international wines.
Drink Mount Defiance Cidery and Distillery
Local distillery, making and serving bourbon, rum, absinthe, agave spirit, amaretto liqueur, apple brandy, cider, and more. Have a taste on-site, and take away a few bottles for late.
Drink Middleburg Common Grounds
A local favorite — coffee, tea, beer, wine — breakfast sandwiches all day — salads — soup — sandwiches — local providers whenever possible — rotating art gallery of local artists.
Sleep
Stay Briar Patch Bed and Breakfast Inn
Historic property on 47 rolling acres with mountain views. 8 antique-decorated bedrooms in the 200-year-old main house, one-bedroom cottage, 3 bedrooms in a renovated chicken coop building. Host events such as weddings, parties, retreats and meetings for up to 200 people.
Nearby
Bluemont
City / town · 4 listings · 11 mi away
Leesburg
City / town · 31 listings · 14 mi away
Ashburn
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Centreville
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Berryville
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Herndon
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My experience
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