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Founded in 1787, cozy, quaint and historic Middleburg
today has a collection of unique shops and restaurants far out of proportion
with what you might expect in a community of 650 people.
Visitors often compare the village and its stunning
surrounding landscape to a beautiful English-countryside vista.
With more than 160 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.
Martha Mason Semmes, town administrator, says, “People in
the town are warm and caring. We have the reputation of being a very
high-end-income area, but the town is very diversified. We do have a large
commercial base compared to the number of people in town, but we are a major
tourist attraction because of our beautiful area and events.”
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 nearby mountains.
Vineyards abound in a climate that yields impressive
wines. In every direction, one sees that only a rich and complex history
could produce such beauty. Middleburg is now and has long been one of the
country’s rare jewels.
“It’s a small town where everyone knows each other, but
it has a world-class reputation as a wonderful place to work and live. We
get visitors from all over the world and we strive to make them welcome to
our historic town,” says Mary Kay Garwood, director of the Pink Box Visitor
Center, who has spent the past 20 years helping visitors become acquainted
with all of the town’s and nearby attractions.
For shopping enthusiasts, Middleburg offers a treasure
trove of variety, quality and distinction. Elegant boutiques in historic
buildings offer goods from the United States and abroad, all carefully
hand-selected by proprietors who operate their shops with pride in their
wares. There are 250 businesses in the town.
Mayor Betsy Allen Davis
Betsy Allen Davis, lifelong resident, has a dual role in
the community. She has been mayor for the past five years and is office
manager of The Fun Shop, which has been family-run since 1956. The business
has served the Middleburg community and visitors from all over the world in
“I love the town’s size, its people, and being in the
heart of the hunt country — not in the middle of an overly crowded big-city
business area. We have the reputation of being the place where if we don’t
have it, you probably don’t need it.” says Davis.
Davis says it was only at the last minute that she
decided to run for the office of mayor, pledging to “represent all the
people and, hopefully, to continue to run the town the way it has been run
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 ambience. The young and young-at-heart are treated to fashion-forward
trends in all aspects of personal attire and one-of-a-kind items for the
A popular stop in the town is the Creme de la Creme, a
shop managed the past 10 years by Manuel Simpson, and offering unique
specialty items ranging from table linens to pottery.
“There hasn’t been a day that I haven’t looked forward to
coming to the store. People who come in are so nice. I can’t see why anyone
would ever want to leave the town.”
Simpson takes time from his shop to volunteer to run the
annual Salvation Army Kettle Drive during the holiday, recruiting some 300
residents to ring the bell. The volunteers normally raise upwards of $8,000
Lisa Capraro is owner of Betsey, a young contemporary
women’s clothing store. It is among the newest businesses in Middleburg,
opening less than a year ago.
“The response from other businesses in the community has
been fantastic. We all work together to help one another,” notes Capraro.
She formerly worked for the town of Leesburg in the historic preservation
area, but had always wanted to be a store owner, and “Middleburg offered me
a great opportunity.”
Visitors can enjoy organic and gourmet markets and tours
of local wineries. Middleburg’s numerous restaurants have something for
every appetite and budget. Visitors can settle in for a leisurely meal in a
historic, romantic setting, or take a quick break for casual fare indoors or
Among the 15 eateries in the town, the best known is the
Red Fox Tavern & Inn, dating to 1728 and listed on the National Register of
Owner Dana Reuter notes that the inn has served as a
prominent landmark in the heart of Middleburg since early in the town’s
“We have 14 rooms and the restaurant seats 200, serving
breakfast, lunch and dinner with our crab cakes and fresh meats and
vegetables being longtime traditional favorites among our customers,”
according to Reuter.
Market Salamander is another Middleburg destination
restaurant, offering a delightful indoor cafe, courtyard or outdoor
cobblestone patio for a relaxing breakfast, lunch or dinner in the charming
Cuisine Vaughn Skaggs
Chef de Cuisine Vaughn Skaggs is the backbone of the
market, noting that the facility offers “award-winning crab cakes as well as
fresh salads and sandwiches to eat in, or the catering department will
create a menu for any event and bring it to your home, office or other
location. We also have a wide selection of Virginia wines,” he says.
Horse Country USA
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.
The town has earned a reputation as the “Nation’s Horse
and Hunt Capital,” attracting prominent visitors from across the United
States, such as the late Jacqueline Kennedy Onassis.
Established in 1978, Journeymen Saddlers, Ltd., has been
providing belt, boot and saddle repairs to horse riders in its shop.
Slim Berg has worked in the shop for 22 years,
specializing in saddle repairs.
“I enjoy the freedom and solitude the job offers. I also
like living in Middleburg, which is ideally located — from here you can
quickly go to Washington, D.C., the Shenandoah Valley and the ocean, where I
enjoy boating, fishing and snorkeling — plus, the town has every kind of
restaurant you would ever want,” says Berg.
Travel Stop Turned Destination
Since the 1700s, Middleburg has been a staging point for
weary travelers along the Ashby Gap Road. Later, the town began welcoming a
new wave of visitors that arrived for fox-hunt and steeple-chase events.
Over the years, Middleburg has maintained its status as a premier
To welcome visitors and cater to their needs, there are
various inns in and around the town, which have hosted everyone from Civil
War officers and soldiers to high-ranking statesmen, government officials,
corporate leaders and celebrities.
JoAnn and Kevin Hazard are the innkeepers for Middleburg
Country Inn, which is adjacent to dozens of unique shops and restaurants all
within walking distance of the Inn.
“There is a place inside all of us that welcomes a warm
smile, the aroma of cookies baking, a snug bed on a glorious morning in
Middleburg — a timeless place where genteel charm and an ageless spirit seem
to fill the very air,” says JoAnn.
is on Tryst for a workout at the Fox Chase
Farm near Middleburg.
She adds, “We just love the town and welcome visitors
with the same warmth and hospitality we have always shared with our friends
and family.”Norman Myers, a real estate appraiser and consultant,
says he has found the town to be very pedestrian friendly.
“I like walking down the streets and smelling the aroma
of the food being prepared in the restaurants. 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 or a brief excursion,” says Myers.
For much of its history, Middleburg had been a
stopping-off point on the way to somewhere else, but its contemporary
transformation has made it a destination in its own right.
Serving as a host community for more than 250 years, it
is no surprise that Middleburg, set in the foothills of Virginia’s horse and
wine country, has developed such a high concentration of fine inns, shops
The town has grown from an 18th century coach-stop
village to a bustling modern community, while successfully retaining its
historic small-town ambiance.