Exploring Middleburg, VA
Time needed in this town: 1-2 nights
Middleburg, Virginia is quintessential “horse country” in an extremely well-preserved historic setting. Hundred-acre horse farms. a quaint downtown area with high-end boutique shopping, restaurants, and cafes; wineries dotting the grassy hills, as well as an upscale resort and historic inns all make up what is one of the most picturesque places in Northern Virginia.
The below information is a complete guide of the best places to stay, the top rated places to dine and drink, and all there is to see and do. We’ve also included transportation tips, as well as the history of this picture-perfect town.
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Where to Stay
Salamander Resort & Spa is my go-to in Middleburg every single time I decide to stay overnight. Their rooms are luxurious and their spa, even more so. But what sets it apart is how it feels. You very much feel like you’re “weekending” in someone’s beautiful home, rather than staying at a hotel.
Some tips for an amazing weekend there:
Play a board game or read a book in the library, which is 24 hours. Note, you are able to order snacks and drinks from there.
Book a spa appointment to get access to the adults-only pool and definitely order from their lunch menu. Also, if you have never used the “seasonal” shower, make sure you do that, too. TIP: They regularly offer discounted spa packages, so check their spa site, often.
Book a trail ride, a zip line adventure, tee time, cooking class, and more! The resort has so many incredible activities to choose from.
Go to the Gold Cup Bar and purchase the s’mores kit. The marshmallows are handmade and are perfect for use with the outdoor fire pits!
Dine at Harriman’s Grill (see our “Where to Dine & Drink” section for more on this.
Other recommendations
Red Fox Inn and Tavern
Where to Dine & Drink
Cuppa Giddy up
Organic and fair trade coffees and espresso. Family owed since 2001. Locally sourced pastries and bagels.
Fields of Athenry Farm & Side Saddle Bistro
They believe in healthy eating as the first and foremost preventative to many illnesses that are a result of a reliance on convenient and processed foods. They sell fresh fresh meats, prepared meals, bone broths, as well as many other goods. They also have a bistro.
Goodstone Inn Bistro
Serving all meals in a causal country setting.
Goodstone inn Conservatory
Experience the ultimate in fine dining in a stunning glass-enclosed dining area that boasts spectacular views of the Hunt Country scenery.
Harrimans Grill
Salamander Resort’s dining room, serving locally-inspired American fare in a country setting.
King Street Oyster Bar
True to its name, they offer various oysters.
Knead Wine
Serving pizzas and bottles of wine. NOTE: They do have gluten-free crust.
Middleburg Deli
Made-to-order sandwiches, salads, and more. It’s great for a picnic lunch on the grounds of Salamander Resort!
Mt. Defiance Cidery and Distillery
Local cider & spirits tastings, plus specialty cocktails, offered in a modern, lofty room.
Red Bar Sushi and Best Thai Kitchen
Serving sushi and thai dishes.
Scruffy’s Ice Cream Parlor
An ice cream parlor in the heart of downtown Middleburg.
The Red Fox Inn & Tavern
Per their site, “An intimate Tavern setting offering a seasonal four course game and seafood dinner experience and extensive beverage menus.”
Tremolo Bar
Per their site, “We are a modern wine bar in historic Middleburg serving impeccable drinks, premium coffee, and internationally-inspired small plates.”
Things to See & Do
Historical Exploration
Aldie Mill
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.
National Sporting Library & Museum (NSLM)
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.
Shopping
Chloe’s of Middleburg
Founded in 2019 by Wendy Osborn, a Rhode Island School of Design graduate and former buyer for Bergdorf Goodman, Chloe's of Middleburg opened with a mission to bring fresh and dynamic fashion to women of all seasons.
The boutique offers classic and fashion-forward apparel, accessories and gifts at affordable prices. Chloe's believes in community, kindness and warmly welcomes all to enjoy a unique shopping experience from the heart of Virginia's hunt country.
Creme de la Creme
A curated collection of French and Italian inspired objects, tableware, and gifts. NOTE: It’s my favorite store in Middleburg! I’ve found Hermés trays, Chanel matchboxes, agate coasters, rustic signs, and local art.
Etten’s Eden
While their focus is on native perennials, they have expanded their offerings to include aquatic plants, annuals, and herbs.
Every Little Something
Every Little Something is a designer and printer of luxury stationery and event invitations. Every Little Something is a world-renowned studio known for high-end designs and attention to detail.
Federal & Black
Located in the historic town of Middleburg, Federal & Black is a standout home decor and gift shop in the heart of Virginia Hunt Country. A thoughtfully curated collection of antique and new goods for your home and garden as well as gifts.
Raymer’s Homemade Candies
Raymer's Homemade Candies is a family-run business, using only pure Belgian Chocolate in their creations.
The Accidental Peacock
They sell antiques, vintage, and curated finds for the home.
The Christmas Sleigh
A unique shop specializing in handmade European gifts, art, and holiday wares. Authentic German, Austrian, and Irish apparel for the whole family. Five rooms chock full of European treasures. Come experience the magic!
Unique Experiences
Christmas in middleburg
There is no more magical place to be for Christmas than in Middleburg! During the end of the first week in December, fun-filled family festivals include family-friendly activities, special events, great eats, the famous Middleburg Hunt Review, and a mile-long Christmas parade. Afterwards, experience a Middleburg evening in one of their bistros, cafes, pubs, and restaurants joining in the Spirits of Middleburg. NOTE: It’s a great time to book that stay at The Red Fox Inn or Salamander Resort.
International Gold Cup
Steeplechasing in Virginia has been a way of life since early Colonial times when the horse was the primary way of transportation, farming, and war. George Washington and Thomas Jefferson met in sporting competition over fences. Organized steeplechase races have run in Fauquier County, since 1844, originally at White Sulphur Springs then a fashionable spa near Warrenton.
On April 3, 1922, eight sportsmen met at the Fauquier Club in Warrenton and decided to organize a four-mile race, between flags, over the natural walls and fences of the nearby hunting countryside. Pledging $1,000 to purchase a trophy for the winning owner, they ruled that it be kept permanently by the first owner to win the race three times, not necessarily in consecutive years, nor with the same horse. Just 34 days later, they held the first Virginia Gold Cup race.
Today, it is held twice a year with nearly 50,000 people in attendance.
Middleburg Film Festival
Each October, Middleburg hosts an annual 4-day film festival, taking place throughout the town A carefully curated selection of films, screened in intimate theatre venues, followed by fascinating Q and A’s with world-renowned filmmakers, actors, and other special guests. Films include Academy Award contenders, first-class foreign language films, independent gems, and riveting documentaries. Other highlights include a concert honoring a renowned film composer or songwriter, 'Wine & Conversation' at local wineries, 'Fireside Chats' with filmmakers and actors, farm-to-table dinners, and parties. The festival draws filmgoers from all over the world and is now recognized as one of the 'stops on the road to the Oscars’.
Wineries
Boxwood estate winery
Boxwood Winery is located in an area steeped in Revolutionary and Civil Wars’ American history and renowned for world-famous horse farms. Today, the area is also known as a wine region, making Virginia 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.
Cana Vineyards & Winery
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.
The 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.
Chrysalis Vineyard
Chrysalis Vineyards is about growing Norton, along with other tested European varieties, which thrive in their soils and climate. Their mission is to produce wines of such distinction that they stand solely on their own merits as world-class wines.
A History Summary
1728 - Joseph Chinn, who was the cousin of George Washington, established a fieldstone tavern (The Red Fox Inn) on an old Native American trail.
1730s - The town had been a staging point for weary travelers along the Ashby Gap Road.
1763 - American Revolutionary War Lieutenant Colonel and Virginia statesman, Leven Powell, purchased the land for Middleburg at $2.50 per acre from Joseph Chinn, a first cousin of George Washington.
1787 - The town was established. It had been called "Chinn's Crossroads" and was then called “Powell Town”. When Leven Powell declined to have the town named after him, the town was called '“Middleburgh”, and later, simply “Middleburg”.
1863 - Middleburg witnessed two skirmishes during the Gettysburg Campaign of the Civil War, the second of which decimated the town. The “Burning Raid” (as it was called) took place over 5 days. The Union Army killed 6,000 cattle, 4,000 sheep, and 600 horses. It also burned down 230 barns, 8 mills, and 25,000 bushels of grain. It took 60 years to recover from it.
1908 - Middleburg began welcoming visitors who participated in foxhunting and steeplechasing.
1960s - Middleburg became known as the equestrian and hunting center of the country which led to an influx of wealth and prosperity. President John F. Kennedy and his family began coming to Middleburg as a weekend getaway from the hustle and bustle of Washington D.C.