Middleburg was established in 1787 by American Revolutionary War Lieutenant Colonel and Virginia statesman John Leven Powell, who purchased the property from Joseph Chinn. 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.
Today it is home to almost 700 people and thriving tourist and equine industries. It is still full of beautiful old homes set amid scenic, rolling countryside filled with horse and dairy farms. Middleburg is home to several fox hunts, including the Middleburg Hunt which holds an annual Christmas Parade through the town.
Middleburg offers a wide variety of homes to choose from, from efficiency apartments downtown, to single family homes around town, to multiple acre homesites and farms. Check it out by search for ZIP code 20117.
Things to do in Middleburg include:
50 West Vineyards
100% Virginia wine in the beautiful rolling hills of Middleburg, Virginia. 50 West specializes in red and white wines produced in the classic Bordeaux style of France and offers stunning views of the Bull Run Mountain range.
Address: 39060 John Mosby Hwy., Middleburg, VA 20117
Phone: 571-367-4760
Aldie Mill
Built between 1807 and 1809, the Aldie Gristmill was once the largest factory of its kind in Loudoun County. Tours and demonstrations are available during weekends between April and November.
Address: 39401 John Mosby Hwy., Aldie, VA 20105
Phone: 703.327.9777
novaparks.com/parks/aldie-mill-historic-park
Best Thai Kitchen
Best Thai Kitchen is a family-owned Thai restaurant that loves to serve delicious, authentic Thai dishes. The secret to their food is in the sauces and the hours of preparation that goes into many of their dishes.
Address: 4 E. Federal St., Middleburg, VA 20117
Phone: 540.326.8111
Boxwood Estate Winery
Boxwood Estate Winery, the winery produces red wine in three styles in the Bordeaux tradition from: Cabernet Franc, Cabernet Sauvignon, Merlot, Petit Verdot and Malbec.
Address: 2042 Burrland Ln., Middleburg, VA 20117
Phone: 540.687.8778
Briar Patch Bed & Breakfast Inn
Stay in one of their 8 antique-decorated bedrooms in the 200-year-old main house, in a one-bedroom cottage, or in one of the three bedrooms in their new chicken coop building. They also host events such as weddings, parties, retreats and meetings for up to 200.
Address: 23130 Briar Patch Ln., Middleburg, VA 20117
Phone: 703.327.5911
The Club at Creighton Farms
Jack Nicklaus Signature golf Course. Opened in 2007, the course is recognized as one of the premier golf courses in the east with elegant dining and reception facilities, intimate rooms for private gatherings, outdoor terrace and patio–and even club rooms for overnight.
Address: 22050 Creighton Farms Dr., Aldie, VA 20105
Phone: 703.957.4800
Gentle Harvest
Specialty grocer and fast-casual farm market restaurant located in Marshall, Virginia.
Address: 8372 W. Main St., Marshall, VA 20115
Phone: 540.837.4405
Glenwood Park
The thousands of race goers come to Middleburg each April for the Middleburg Hunt Races. The Middleburg Spring Races is the oldest Steeplechase racing in Virginia. It is almost 100 years old.
Route 626, Foxcroft Road, Middleburg, VA 20117
+1 540-687-6545
Gold Cup Wine Bar
Gold Cup Wine Bar features small plates of Piedmont-inspired cuisine paired with featured Virginia and international wines.
Address:500 N. Pendleton St., Middleburg, VA 20117
Phone: 540.751.3164
Goodstone Inn & Restaurant
Set on a 265-acre estate in the heart of Middleburg’s wine and hunt country, features state-of-the-art, seasonally-inspired cuisine with a farm-to-table emphasis.
Address: 36205 Snake Hill Rd., Middleburg, VA 20117
Phone: 540.687.3333
Greenhill Winery & Vineyards
Authentic Virginia wine and hunt country setting.
Address: 23595 Winery Ln., Middleburg, VA 20117
Phone: 540.687.6968
Harrimans Virginia Piedmont Grill
Harrimans menu highlights fresh, seasonal ingredients, captivating farm to table elements with their very own chef’s garden located just outside the restaurant.
Address: 500 N. Pendleton St., Middleburg, VA 20117
Phone: 540.326.4070
Hunter’s Head Tavern
Hunter’s Head Tavern is an authentic English Pub that serves pub fare, fine dining cuisine and mouthwatering homemade desserts.
Address: 9048 John S. Mosby Hwy., Upperville, VA 20184
Phone: 540.592.9020
King Street Oyster Bar
King Street Oyster Bar specializes in bringing fresh oysters from both the West and East Coasts of the US and Canada to the communities we call home.
1 East Washington St,
Middleburg, VA 20117
(540) 883-3156
Market Salamander
Market Salamander is a working chef’s gourmet market.
Address: 200 W. Washington St., Middleburg, VA 20117
Phone: 540.687.8011
Middleburg Common Grounds
Middleburg Common Grounds serves coffee, tea, beer and wine, as well as breakfast sandwiches all day, salads, soup and sandwiches using local providers of ingredients whenever possible.
Address: 114 W. Washington St., Middleburg, VA 20117
Phone: 540.687.7065
Middleburg Community Center
Enjoy the picnic grounds, garden, playgrounds, pool and other outdoor spaces. Sign up for a class, or stop in at one of their many public events.
Address: 300 W. Washington St., Middleburg, VA 20117
Phone: 540.687.6373
Middleburg Ghost Tours
Enjoy a leisurely stroll through quaint Middleburg, Virginia’s haunted history. Per square acre, it has documented history and more reported “strange” occurrences than any other town in the US.
P.O. Box 1745
Middleburg, VA 20118
(540) 836-3152
http://middleburgghosttours.com/
Mount Defiance Cidery & Distillery
Mt. Defiance creates handcrafted, small batch hard cider and spirits. We are located in historic downtown Middleburg, Virginia. Tastings of our ciders are always available.
207 W Washington Street, Middleburg, VA 20117
+1 540-687-8100
National Sporting Library & Museum
Founded in 1954, the renowned research library and fine art museum highlight the rich heritage and tradition of country pursuits.
Address: 102 The Plains Rd., Middleburg, VA 20117
Phone: 540.687.6542
Popcorn Monkey
Family-owned gourmet popcorn shop specializes in handmade, fresh popcorn in small batches. They offer a full line of sports popcorn tins, cinnamon glazed nuts, retro candy and more.
Address: 101 W. Federal St., Middleburg, VA 20117
Phone: 540.687.6539
Red Fox Inn & Tavern
Offers 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.
Address: 2 E. Washington St., Middleburg, VA 20117
Phone: 540.687.6301
Salamander Resort & Spa
Features luxurious guestrooms and spacious suites, a luxury spa, full-service equestrian center, Virginia Piedmont-inspired dining, a multi-experience cooking studio, well-appointed wine bar, billiards room, library, zip lining course, abundant amount of outdoor activities, and an array of conference and banquet facilities.
Address: 500 N. Pendleton St., Middleburg, VA 20117
Phone: 540.687.3600
Side Saddle Café
Offers freshly cut prime beef, lamb, poultry and pork at its gourmet farm shop as well as a full array of breakfast, lunch and dinner items featuring seasonal items with pasture-raised meats, organic produce and homemade breads.
Address: 7 W. Washington St., Middleburg, VA 20117
540-326-8177
The Upper Crust
The Upper Crust is a quaint bakery and café specializing in cookies and pies, with sandwiches and some breakfast options. Home of the famous Cow Puddle Cookie!
Address: 2 N. Pendleton St., Middleburg, VA 20117
Phone: 540.687.5666
https://www.restaurantji.com/va/middleburg/upper-crust-/
Three Fox Vineyards
Boutique winery and vineyard producing hand-crafted, Italian/old-world style wines on 50 beautiful rolling acres reminiscent of Tuscany.
Address: 10100 Three Fox Ln., Delaplane, VA 20144
Phone: 540.364.6073
Want to see more neighboring towns in the community? Check out our pages for Leesburg, Purcellville, and Berryville.
Love this town and want to move here? See available homes for sale and for rent.
