Situated along Route 50 between Winchester and Alexandria and only about 45-minutes from Washington, D.C., the quaint town of Middleburg has a rich history and Southern charm.
The Middleburg area was the Civil War site where two skirmishes took place in 1863. In the 1900s, Middleburg became the go-to place for steeplechasing events and fox hunting and earned its title as the Nation’s Horse and Hunt Capital.
Today around Middleburg, you will find nearly a dozen wineries to sample some of Virginia’s best wines, and the area is known as one of the world’s top ten wine destinations.
If fun is what you are searching for, then spend the day zip lining or horseback riding through the scenic Blue Ridge Mountains, or visit some of the local haunts on the Middleburg Ghost Tour.
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Vineyards Galore
Enjoy the scenery along with the superb wine at one of the numerous vineyards and wineries in the area.
The Boxwood Winery
- Address: 2042 Burrland Ln, Middleburg, VA 20117
The nearly 27-acre Boxwood Winery is a landmark farm that produces Merlot, Cabernet Franc, and lush Bordeaux varietals. Visitors can enjoy a five-wine tasting flight in the cozy tasting room or at the picnic tables outside while listening to live music Thursdays through Sundays. Be sure to try a glass of their outstanding 2015 Reserve.
50 West Vineyards
- Address: 39060 John Mosby Hwy, Middleburg, VA 20117
Visit Mike and Diane Canney’s 50 West Vineyards, where you will find one of the most extensive vineyards in Virginia. From the fields on the bluff, you can enjoy the view of the Bull Run Mountains. At 50 West Vineyards, they use Old World winemaking techniques to craft their 100% Virginia fruit wine. Head to the old horse stable building, which now is home to the winery’s tasting room to enjoy their Chardonnay, Vidal and Sauvignon Blanc, and Albarino wines.
Chrysalis Vineyards at The Ag District
- Address: 39025 John Mosby Hwy, Middleburg, VA 20117
One of the wineries in Middleburg that you must visit is the 70-acre Chrysalis Vineyards at The Ag District. Outside of town along John Mosby Highway, you will find the Chrysalis Vineyard within the 412 acres of Locksley Estate, nestled in the Bull Run Mountains.
Amongst some of the loveliest countryside, you can sit indoors or outdoors and participate in either the Estate or Reserve Tasting and sample some of their unique white or red Norton, Albariño, or Viognier wines.
Besides their award-winning Norton wines, the winery also sells local jams, cheeses, and charcuterie.
Cana Vineyards and Winery
- Address: 38600 John Mosby Hwy, Middleburg, VA 20117
The Cana Vineyards and Winery is a beautiful place to visit while in Middleburg. The family-owned farm on John Mosby Highway between Middleburg and Aldie features a second-floor tasting room overlooking the Blue Ridge and Bull Run Mountains. For those who wish to enjoy their wine tasting outside, there is a porch, heated sun pavilion, and vast lawn where you can enjoy a picnic lunch or dinner while sampling excellent Virginia-made wines.
The passionate work of owners Lisa and Bryce and Winemaker Melanie have earned this five-acre vineyard the title of Virginia Winery of the Year repeatedly at the New York International Wine Competition.
Come out and enjoy the Petit Verdot, Merlot, or award-winning Rosé wines while listening to live music each weekend. The winery is both family and pet-friendly.
Greenhill Winery and Vineyard
The lovely Greenhill Winery and Vineyard is an adult-only boutique winery situated in the Greenhill area of Middleburg. During your visit, take a tour of the property and then head to the farmhouse tasting room, where you can sample quality French-influenced wines made with 100% Virginia grapes, including the Blanc de Blancs.
The grounds are pet-friendly, and you are welcome to bring a picnic to eat in the outside areas.
Before leaving, check out the Farm Store, where you can purchase honey and Charolais beef.
Stone Tower Winery
- Address: 19925 Hogback Mountain Rd, Leesburg, VA 20175
Surrounding the popular Stone Tower Winery are 75 acres of vineyards and offers a variety of places to enjoy sipping a glass of their specialty, Sparkling Rosé wine.
While visiting, head to the Tower Tasting Room, where you can enjoy viewing the distant mountains as you sample seven different wines, including Petit Verdot. The terrace offers visitors picnic tables to sit at while partaking in a picnic lunch, or gourmet pizza and snacks from the Stone Tower paired with a bottle of Stone Tower wine.
More Wineries near Middleburg VA
- The Ag District, 39025 John Mosby Hwy, Middleburg, VA 20117
- Barrel Oak Winery, 3623 Grove Ln, Delaplane, VA 20144
- Magnolia Vineyards, 200 View Town Rd, Amissville, VA 20106
- Quattro Goombas Winery, 22860 James Monroe Hwy, Aldie, VA 20105
- Williams Gap Vineyard, 35521 Sexton Farm Ln, Round Hill, VA 20141
- Goose Creek Farms & Winery LLC, 18050 Tranquility Rd, Purcellville, VA 20132
Nearby Wineries in Leesburg
- Dry Mill Vineyard & Winery LLC, 18195 Dry Mill Rd, Leesburg, VA 20175
- Zephaniah Farm Vineyard, 19381 Dunlop Mill Rd, Leesburg, VA 20175
- Willowcroft Farm Vineyards, 38906 Mt Gilead Rd, Leesburg, VA 20175
- Fleetwood Farm Winery, 23075 Evergreen Ml Rd, Leesburg, VA 20175
- Casanel Vineyards & Winery, 17956 Canby Rd, Leesburg, VA 20175
Breweries, Distilleries, and Cideries to Explore
Lost Barrel Brewing
- Address: 36138 John Mosby Hwy, Middleburg, VA 20117
Lost Barrel Brewing along John Mosby Highway on the west side of town features handcrafted lager, ale, and hard seltzers to drink in the tap house, on the porch, at a picnic table, or on a picnic blanket on the grounds of the countryside location.
Plan on spending a relaxing evening with friends and family sitting in the Adirondack chairs as you sit in the warm glow of the fire in the firepits.
During the weekends, bring a chair or blanket and sit back and listen and dance to the music of local music groups or spun tunes of a DJ.
The Lost Barrel Brewing permits leashed dogs in their outdoor areas.
Mount Defiance Cidery and Distillery
- Address: 207 W Washington St, Middleburg, VA 20117
Since 2014 Mt. Defiance Cidery and Distillery has been recognized for producing handcrafted spirits and hard ciders in Middleburg.
At Mt. Defiance’s Cider Barn, head to the tasting hall to participate in tastings of all their tasty ciders. Their specialty is dry cider infused with fresh ginger, peppers, or co-fermented with blueberries and honey.
Visit the distillery for locally made rum, bourbon, and potent absinthe. At the distillery, they focus on producing all your favorite classic spirits of long ago. Have a seat and enjoy a tasting flight of Colonial-era drinks like apple brandy, amber rum, and straight bourbon whiskey.
Old Ox Brewery Middleburg (Temporarily Closed- 2023)
- Address: 14 S Madison St, Middleburg, VA 20117
While visiting historic Middleburg, stop in at the Old Ox Brewery on South Madison Street for a lager, fruity IPA, or a hearty porter with a touch of chocolate.
Stop at the food truck out front before heading in with your food to the tasting room or beer garden. Here you can enjoy the golden ale Golden Ox, the IPAs Hop Camo, and Hoppy Place, which are always on tap. If those don’t wet your whistle, then try one of the nearly a dozen other limited-time beers on tap.
The beer garden has a beautiful alfresco courtyard that is perfect for relaxing with friends, family, or your dog.
NOTE: They are only open Wednesday through Sunday.
Middleburg’s Art and History Scene
Destination Middleburg: A Walking Tour Into the Past
Besides the beautiful Blue Ridge and Bull Run Mountains, you will discover more than 150 historic buildings in Middleburg. The best way to explore these buildings is to stop by the Middleburg Visitor Center and pick up a copy of the Destinations Middleburg: A Walking Tour Into the Past.
As you stroll the streets of Middleburg, the self-guided stroll begins at the Middleburg Visitor Center and takes you past 52 buildings in roughly 1½ hours.
National Sporting Library and Museum
- Address: 102 The Plains Rd, Middleburg, VA 20117
- Details
The 6-acre complex within Virginia’s prime hunting area lies a world-class research library and fine art museum where you can find rare books, archives, and art collections dealing with horsemanship, fox hunting, polo, and wildlife.
Tour the library’s rare book room, participate in educational programs, or participate in family activities throughout the year.
The Sporting Gallery
- Address: 11 W Washington St, Middleburg, VA 20117
- Details
The Sporting Gallery in the historic Duffy House is a must-see destination in Middleburg. Since 1963 the gallery has featured wildlife and sporting oriented artwork and honors Middleburg’s rich hunting and sporting history.
View Peter Sculthorpe’s watercolor landscapes, Linda Volrath’s animal paintings, and an extensive collection of porcelain foxes.
Other Things to do in Middleburg VA
- Aldie Mill Historic Park, 39401 John Mosby Hwy, Aldie, VA 20105
- Middleburg Film Festival (October), Middleburg, VA
- Artists in Middleburg, first floor, 102 W Washington St, Middleburg, VA 20117
- Mount Defiance – Battle of Middleburg (Mt Defiance Historic Park), 35945 John Mosby Hwy, Middleburg, VA 20117
- Middleburg Information Center, 12 N Madison St, Middleburg, VA 20117
- Masters of Foxhounds Museum, 301 E. Washington St., Middleburg, Virginia 20117.
- Middleburg Library, 101 Reed St, Middleburg, VA 20117
Middleburg VA Horses
Since Middleburg is known as the United States’ Horse and Hunt Capital, a trip to Middleburg would not be complete without an equestrian activity or two.
Countryside Group Trail Ride
- Address: Salamander Middleburg Resort and Spa, Equestrian Program, 500 N Pendleton St, Middleburg, VA 20117
There are plenty of places to see horses in Middleburg, but only one easy spot to go horseback riding in town– Salamander Resort and Spa.
You can schedule a guided trail ride, private ride or riding lesson. There are also pony rides for younger kids who might be a bit nervous to hop on a horse.
More Places to see Horses in Middleburg VA
- Middleburg Spring Races, 107 W Federal St #9b, Middleburg, VA 20117
- Twilight Polo Club, 37636 Charisma Ln, Middleburg, VA 20117
Outdoor Adventures in Middleburg VA
Empower Adventures
- Address: 500 N Pendleton St, Middleburg, VA 20117
- Details
While staying at Salamander Resort and Spa or taking a guided trail ride, stay a bit longer and get your adrenalin flowing and take to the treetops with one of Empower Adventures zipline courses.
Middleburg Ghost Tours
- Address: meeting point assigned after purchse
- Details
Spend an eerie Friday or Saturday evening with the guides of Middleburg Ghost Tours. During the walking tour, you will take to the haunted streets of historic Middleburg and discover the fascinating spirit’s stories along the way.
Middleburg Community Center
- Address: 300 W Washington St, Middleburg, VA 20117
- Details
The kids will want to spend at least an hour or two at the Middleburg Community Center’s pool on a hot summer day. The pool is open from Memorial Day weekend through Labor Day, and you do not need to be a resident of Middleburg to splash around.
The Community Center also has beach volleyball courts, a baseball field, and two playgrounds.
If you are looking for a spot to cook hotdogs or hamburgers for dinner, head to the shady picnic area, fire up the bbq grill, and enjoy a picnic.
Boutique Shopping in Middleburg
Stroll along Middleburg’s brick sidewalks and peruse some of the stylish boutiques and unique gift shops. During the first week of August, Middleburg holds the summer Sidewalk Sales, where you can find great bargains along the brick sidewalks
Highcliffe Clothiers
- Address: 112 W Washington St #101, Middleburg, VA 20117
- Why we love it: Tailored clothes for men and women
The Fun Shop
- Address: 115 W Washington St, Middleburg, VA 20117
- Why we love it: Toys, books, horse memorabilia, and more.
Christmas Sleigh, Inc.
- Address: 5 E Washington St, Middleburg, VA 20117
- Why we love it: Christmas all year round!
Lou Lou Boutiques
- Address: 18 E Washington St M, Middleburg, VA 20117
- Why we love it: great accessories shop that is local to the DMV
Popcorn Monkey (temporarily closed)
- Address: 101 W Federal St, Middleburg, VA 20117
- Why we love it: Gourmet popcorn
Second Chapter Books (permanently closed)
- Why we love it: new and used books
Restaurants in Middleburg VA
Whatever your budget and tastes, Middleburg has an array of delightful options on where to eat. You will have a superb selection of both local cafés, restaurants, and fine dining establishments.
Middleburg is fortunate to have a wide variety of excellent eateries, with everything from fine dining to a corner café.
Thaiverse
- Address: 101 S Madison St, Middleburg, VA 20117
In my experience, for an excellent Thai dinner, you will want to walk through Thaiverse’s foyer and pass the Kaffir lime tree before entering the well-appointed restaurant to dine on flavorsome dishes and creative cocktails.
Thaiverse has won many top awards in Washington DC, including #1 Best Overall Restaurant 2017 by Dinners’ Choice Awards and #1 Asian Restaurant in 2019 by Open Table.
Reservations are HIGHLY recommended, especially on weekends.
Breakfast and Coffee
Middleburg Common Grounds
- Address: 114 W Washington St, Middleburg, VA 20117
Cuppa Giddy Up
- Address: 8 E Washington St, Middleburg, VA 20117
The Upper Crust
- Address: 4 N Pendleton St, Middleburg, VA 20117
The Upper Crust features delicious fresh baked goods, including their famous cow puddle cookies.
Lunch and Dinner Options
Side Saddle Bistro
- Address: 7 W Washington St, Middleburg, VA 20117
- Why we like it: farm-to-table meats
King Street Oyster Bar
- Address: 1 E Washington St, Middleburg, VA 20117
- Why we like it: Fresh oysters during happy hour at
Red Fox Inn
- Address: 2 E Washington St, Middleburg, VA 20117
- Why we like it: this is the place to go for crab cakes, Virginia peanut soup, and southern dishes
Red Bar Suski
- Address: 4 E Federal St, Middleburg, VA 20117
- Why we like it: Add a little Asian spice to your dinner at the
Market Salamander
- Address: 200 W Washington St, Middleburg, VA 20117
- Why we like it: Need a sandwich on the go, head to
Gold Cup Wine Bar
- Address: 500 N Pendleton St, Middleburg, VA 20117
- Why we like it: offers formal dining and a locally inspired menu
Harrimans Virginia Piedmont Grill
- Address: 500 N Pendleton St, Middleburg, VA 20117
- Why we like it: features ‘Not Your Mother’s Pork Chop’ and a 22-ounce ribeye
Goodstone Inn and Restaurant
- Address: 36205 Snake Hill Rd, Middleburg, VA 20117
- Why we like it: features farm-to-table cuisine and was voted one of the top Virginia restaurants. Choose from over 800 bottles of international wine.
Luxurious Resorts, Historic Inns, and Bed and Breakfast Choices
Middleburg does have an array of places to stay, but you may want to step it up a notch or two and enjoy one of Middleburg’s classic inns or spend a night or two at one of the luxury resorts in town.
The Red Fox Inn and Tavern
- Address: 2 E Washington St, Middleburg, VA 20117
- Details
The romantic guest rooms at the must-visit Red Fox Inn & Tavern have featured local Piedmont furnishings since opening in 1728.
Since opening nearly 300 years ago, the inn has had many celebrity visitors, including John F. and Jackie Kennedy, Elizabeth Taylor, Tom Cruise, and Paul Newman.
Salamander Resort & Spa
- Address: 500 N Pendleton St, Middleburg, VA 20117
- Details
The 168 guest rooms and suites at the equine-themed Salamander Resort and Spa offer scenic views of the resort and beyond.
The 23,000-square foot health and wellness spa features 14 treatment rooms, an outdoor heated pool, and 25 acres for horseback riding.
You can also enjoy spending time in the billiards room, hiking, playing tennis, and ziplining at the resort.
Not only has the Wall Street Journal named the Salamander Resort and Spa as one of the world’s best spas, but it has also received the Condé Nast Traveler’s Readers’ Choice Award and was awarded 5-Star by Forbes Travel Guide.
Goodstone Inn and Restaurant
- Address: 36205 Snake Hill Rd, Middleburg, VA 20117
- Details
The Goodstone Inn and Restaurant have been named one of the United States’ 10 best romantic inns by USA Today and an excellent North American inn by Condé Nast Johansens.
During your stay on the 265-acre property, you will be sue to enjoy the luxury amenities and stunning views that come with each of the 18 elegant guest rooms. The historic cottages across the estate are individually decorated and feature romantic English and French décor.
Begin or end each day of your stay with a stroll or bike ride along the two miles of trails and soothe your muscles in the heated pool and hot tub.
At mealtime, visit the Conservatory restaurant where you can experience Chef Jan Van Haute’s Farm-to-table tasting menu or French entrees like butternut squash, lamb loins, and scallops.
Briar Patch Bed and Breakfast
- Address: 23130 Briar Patch Ln, Middleburg, VA 20117
- Details
Just out of town, you will find one of Middleburg’s most elegant Bed & Breakfast. The Briar Patch Bed and Breakfast sits amongst 47 acres of horse country. Choose between staying in one of the eight bedrooms in the main house or a separate cottage. All the rooms are named after flowers on the property and furnished with antiques.
For those that enjoy cooking, book your stay during one of the cooking class weekends, where you will learn to prepare a four-course gourmet meal.
The B&B is dog-friendly.
Middleburg VA FAQ
Where is Middleburg, VA located?
Middleburg is a town located in Loudoun County, Virginia, in the United States. It is about 50 miles west of Washington, D.C.
What is Middleburg known for?
Middleburg is known for its beautiful scenery, equestrian events, historic sites and battlefields, and upscale shopping and dining experiences.
What are some popular attractions in Middleburg?
The National Sporting Library & Museum, the Middleburg Historic District, the Red Fox Inn & Tavern, and the Salamander Resort & Spa are some of the top spots to check out, but there are plenty of horse-centric events to experience too.
In my experience, Twilight Polo is one of the unique things you can do in Middleburg, especially if you are new to the equestrian scene. Make sure you grab tickets early… and pack a picnic.
What equestrian events take place in Middleburg?
Middleburg is home to several equestrian events throughout the year, including the Middleburg Spring Races, Twilight Polo, the Virginia Gold Cup, and the Middleburg Hunt & Country Fair.
What is the best time of year to visit Middleburg?
Spring and fall are popular times for equestrian events (and checking out the wineries during harvest), while summer is a great time for outdoor activities and exploring the town’s shops and restaurants.
Winter brings holiday festivities, including the famous Middleburg Christmas parades that includes horses and hounds. People from all over drive into MIddleburg to line the streets and watch this parade.
Are there any outdoor activities to do in Middleburg?
Yes, Middleburg is home to hiking, biking, horseback riding, and exploring the town’s parks, hostoric battlefields and nature preserves.
What are some of the best restaurants in Middleburg?
Some of the best restaurants in Middleburg include the Red Fox Inn & Tavern, Market Salamander, and Harrimans Virginia Piedmont Grill.
Are there any wineries or breweries in Middleburg?
There are several wineries and breweries in Middleburg, including Greenhill Winery & Vineyards, Boxwood Winery, and 50 West Vineyards.
Is Middleburg a good place to stay for a weekend getaway?
Yes, Middleburg is a great place for a weekend getaway, with plenty of activities and attractions to keep you entertained. There are plenty of luxury hotels in Middleburg, including the Salamander Resort & Spa and the Goodstone Inn & Restaurant, and spas to find your zen and relax.
