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Upon discovering the village of Middleburg and the stunning surrounding landscape, visitors frequently draw comparisons to the beautiful English countryside. Home to the National Sporting Library and with more than 160 historic buildings listed on the National Register of Historic Places and the Virginia Landmarks Register, Middleburg is synonymous with history and charm. Here, the very best of our nation’s past meets the style, substance and creativity of the 21st century. The result is a remarkable escape from the ordinary.
Low stone walls gracefully wind through pristine fields that stretch to the horizon. Picturesque farms provide tranquil settings for some of the finest horses in the country. Cattle graze in rolling pastures against a backdrop of the nearby Blue Ridge and Bull Run mountains. Vineyards abound, enjoying the perfect climate for grapes that yield impressive wines. From every direction one looks, it is evident that only a rich and complex history could produce such beauty. Middleburg is now and has long been one of the country’s rarest jewels.

For shopping enthusiasts, Middleburg offers a treasure trove of variety, quality and distinction. Elegant boutiques in historic buildings present the best collections from the United States and abroad. Here one finds goods from the United States and abroad, all carefully hand-selected by proprietors who run their shops in the time-honored tradition of extreme pride in their wares.
The shops are replete with character and are brimming with world-class art, clothing, jewelry, home furnishings, antiques and books. Middleburg consistently upholds its heritage and the shops accordingly contain a multitude of items that reflect the refinement of upscale country living and the finest objects from bygone eras. Additionally, the village successfully incorporates a modern point of view. Both the young and the young at heart are treated to fashion-forward trends in all aspects of personal attire and appointments for the home.
Middleburg also offers a wide array of practical items and services for all occasions. Those with a love of botanicals will find extraordinary floral galleries. Animal lovers are thrilled by the countless products for and about horses, cows, dogs and cats. Talented tailors create bespoke clothing and first-in-class saddlers outfit the equestrian community. Shoppers delight in affordable but one-of-a-kind gifts.
Visitors with a passion for food and drink can peruse organic and gourmet markets as well as enjoy tours of local wineries. Additionally, Middleburg’s numerous restaurants have something for every appetite and budget. Visitors can settle in for a leisurely meal in an historic, romantic setting or take a quick break for casual fare indoors or al fresco.
During the holidays, Middleburg is beautifully decorated with storefronts and street lamps festooned with greenery and lights. The annual Christmas in Middleburg celebration begins with the Middleburg Hunt’s hounds leading horses and riders in full attire through the center of the town. Later in the day, the parade, complete with bands and floats, draws hundreds of people who gather to participate in this splendid and most unusual event.
As an equestrian mecca, Middleburg provides the setting for many horse-related events. Glenwood Park, a spectacular center that dates back to 1911, hosts year-round equestrian activities. Just down the road, The Upperville Colt & Horse Show, the oldest horse show in America, is held in early June and brings riders from across the nation. The annual Memorial Day Weekend Stable Tour provides a rare opportunity for visitors to tour the exquisite stables that grace Middleburg’s finest estates.
Middleburg was established in 1787 by Revolutionary War Lieutenant Colonel and Virginia statesman Leven Powell. He purchased the land for Middleburg at $2.50 an acre from Joseph Chinn, first cousin to George Washington. Previously called “Chinn’s Crossroads,” Powell chose the name Middleburg because of the town’s location midway between Alexandria and Winchester on the Ashby Gap trading route (now Route 50).
Since the 1700s, Middleburg has been a staging point for weary travelers along the Ashby Gap Road. Later, Middleburg began welcoming a new wave of visitors that descended on the town for foxhunting and steeplechasing. Over the years, Middleburg has maintained its status as a premier destination. To welcome visitors and cater to their needs, Middleburg has many inns in and around the town, all of which have fascinating histories and some of which have hosted everyone from Civil War officers and soldiers to high-ranking statesmen, government officials, corporate leaders and celebrities.
Middleburg is not only an ideal haven for couples, it is also extremely family- and pet-friendly. Its convenient location, just one hour from downtown Washington, D.C., and 35 minutes from Washington Dulles International Airport, makes it the perfect spot for a multiple-day vacation as well as a brief excursion.
Many national and international visitors return frequently to Middleburg, taking full advantage of the opportunity to relax, enjoy the resplendent countryside and be part of a magnificent place that is so very close and yet so far from the everyday.
There are approximately 600 people currently residing in the town established in 1787 by Revolutionary War Lieutenant Colonel and Virginia statesman, Leven Powell. He purchased the land for Middleburg at $2.50 an acre from Joseph Chinn, first cousin to George Washington. Previously called "Chinn's Crossroads," Powell chose the name Middleburg because of the town's location midway between Alexandria and Winchester on the Ashby Gap trading route (now Route 50).
Since the 1730s, Middleburg had been a staging point for weary travelers along the Ashby Gap Road. The legacy of the colonial era continues today at Middleburg's charming inns that provide first rate accommodations to visitors from around the world.
There are several inns located within the corporate limits, including the historic Red Fox Inn and Tavern. It is billed as the "oldest original inn in America," The Red Fox Tavern was a meeting spot for Confederate Colonel John Mosby and his Rangers. A century later, President Kennedy's press secretary, Pierre Salinger, held press conferences at the Red Fox in the Jeb Stuart room.
Across the street is another gracious reminder of the past, the Noble House, circa 1824. During the Civil War it was known as the Colonial Inn and was run by Catherine Broun. Although Catherine sympathized with the South, she generously served meals to Union troops at the inn as well when they occupied Middleburg in 1862.
After the turn of the century, Middleburg began welcoming a new wave of visitors that descended on the town for foxhunting and steeplechasing. The charming village soon earned a reputation as the "Nation's Horse and Hunt Capital," attracting prominent visitors from across the United States.


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