Destination Main Streets

Middleburg, Virginia

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Middleburg, Virginia got its name due to its midway point on the Ashby Gap Trading Route, which ran between Alexandria and Winchester. But you could also imagine the name coming from its idyllic location in the middle of Virginia's Hunt Country. Known for its large estates, hunting grounds, and vineyards, the town of Middleburg is the center of this part of Virginia's pastoral charms. In fact, many of the shops and restaurants are themed after the legendary fox hunts the area was once known for.

Today the Ashby Gab Trading Route is better known as U.S. Route 50 and as it travels through Middleburg it becomes Washington Street, the town's Main Street. Middleburg, Virginia is located in southern Loudoun County in Northern Virginia. Middleburg is approximately 45 miles away from Washington, DC by way of U.S. Route 50, which will take you all the way into the heart of Middleburg. Other Main Street areas nearby include Leesburg, which is also in Loudoun County, Manassas, and Warrenton.

Photo Gallery

We start our tour of Middleburg, Virginia on the east end of Washington Street and will work our way west.  Most of Middleburg's historic district follows along Washington Street, which is Middleburg's Main Street.
We start our tour of Middleburg, Virginia on the east end of Washington Street and will work our way west. Most of Middleburg's historic district follows along Washington Street, which is Middleburg's Main Street.
Some historic brick structures along Washington Street.  US Route 50 becomes Washington Street as it runs through Middleburg.  It's interesting to note because US Route 50 runs across America from Ocean City, Maryland on the Atlantic Coast all the way to Sacramento, California for over 3,000 miles.
Some historic brick structures along Washington Street. US Route 50 becomes Washington Street as it runs through Middleburg. It's interesting to note because US Route 50 runs across America from Ocean City, Maryland on the Atlantic Coast all the way to Sacramento, California for over 3,000 miles.
As you can see there's plenty of parking along Washington Street, just don't forget to pay the meters.  The Emmanuel Episcopal Church holds an annual Christmas Shop.
As you can see there's plenty of parking along Washington Street, just don't forget to pay the meters. The Emmanuel Episcopal Church holds an annual Christmas Shop.
A deli occupies the northwest corner of Washington Street and Liberty Street.
A deli occupies the northwest corner of Washington Street and Liberty Street.
Shoppers browse the various boutiques that occupy the historic buildings that line Washington Street in historic Middleburg, Virginia.
Shoppers browse the various boutiques that occupy the historic buildings that line Washington Street in historic Middleburg, Virginia.
This is interesting.  Head south on Liberty Street and you'll find a book store attached to public restrooms.
This is interesting. Head south on Liberty Street and you'll find a book store attached to public restrooms.
We head back to Washington Street where we find some more shops.  This one has what appears to be a cicada on its sign.
We head back to Washington Street where we find some more shops. This one has what appears to be a cicada on its sign.
More boutiques and a wide variety of architecture across the street on Washington Street.
More boutiques and a wide variety of architecture across the street on Washington Street.
And looking back again on the other side of Washington Street.  It was early in the evening when we were taking pictures so some of the shops were starting to close.
And looking back again on the other side of Washington Street. It was early in the evening when we were taking pictures so some of the shops were starting to close.
A picturesque view of Washington Street in Middleburg, Virginia.  Probably one of the most scenic portions of U.S. Route 50 in the country.  The town includes many examples of early to mid nineteenth century architecture.
A picturesque view of Washington Street in Middleburg, Virginia. Probably one of the most scenic portions of U.S. Route 50 in the country. The town includes many examples of early to mid nineteenth century architecture.
Clothing boutiques, pet stores, and fine dining line the brick-paved sidewalks along Washington Street.
Clothing boutiques, pet stores, and fine dining line the brick-paved sidewalks along Washington Street.
Another view of the same stretch of Washington Street, this time looking east bound.  The Christmas Sleigh is a Christmas Store and gift shop owned by Linda Tripp.
Another view of the same stretch of Washington Street, this time looking east bound. The Christmas Sleigh is a Christmas Store and gift shop owned by Linda Tripp.
The Red Fox Inn & Tavern dates back to around 1830 and is believed to be one of the oldest continuously operating inns in Virginia.  It features Federal and Colonial Revival details.  It has been remodeled quite a bit.  Notice the metal roof?  Many historic buildings in Middleburg had similar roofs.
The Red Fox Inn & Tavern dates back to around 1830 and is believed to be one of the oldest continuously operating inns in Virginia. It features Federal and Colonial Revival details. It has been remodeled quite a bit. Notice the metal roof? Many historic buildings in Middleburg had similar roofs.
On the corner of Washington Street and Madison Street in what was once a bank is now an organic grocery store, owned by one of the cofounders of Cisco Systems.
On the corner of Washington Street and Madison Street in what was once a bank is now an organic grocery store, owned by one of the cofounders of Cisco Systems.
Heading south on Madison Street, we come across more shops and boutiques, including a wine shop, which only makes sense considering you're in Virginia's wine country.
Heading south on Madison Street, we come across more shops and boutiques, including a wine shop, which only makes sense considering you're in Virginia's wine country.
More shops along Madison Street and more of those metal roofs we were noticing earlier.
More shops along Madison Street and more of those metal roofs we were noticing earlier.
At the corner of Federal Street and Madison Street, this restaurant is paying tribute to Virginia's Hunt Country heritage.
At the corner of Federal Street and Madison Street, this restaurant is paying tribute to Virginia's Hunt Country heritage.
A look at a few more shops before we turn around and head back the way we came.
A look at a few more shops before we turn around and head back the way we came.
We head back up Madison Street and cross over Washington Street and continue north on Madison.  This historic building is called The Pink Box and serves as the Information Center of Historic Middleburg.
We head back up Madison Street and cross over Washington Street and continue north on Madison. This historic building is called The Pink Box and serves as the Information Center of Historic Middleburg.
Nearby is a pavillion "dedicated to the memory of Jacqueline Kennedy Onassis and her happy years in the village."
Nearby is a pavillion "dedicated to the memory of Jacqueline Kennedy Onassis and her happy years in the village."
We finally make it back to Washington Street.  At the intersection of Washington and Madison Streets is the Noble House, built circa 1824, it was once an inn.  Today it houses financial offices and even recently was home to a bank.
We finally make it back to Washington Street. At the intersection of Washington and Madison Streets is the Noble House, built circa 1824, it was once an inn. Today it houses financial offices and even recently was home to a bank.
Across the street is a small boutique with a cupola and weather vane on the roof.  And there's that metal roof again.
Across the street is a small boutique with a cupola and weather vane on the roof. And there's that metal roof again.
A party of young adults are all dressed up and ready for an evening of elegant dining.
A party of young adults are all dressed up and ready for an evening of elegant dining.
Several businesses are located in this historic building with its interesting cut stone.  The Fox's Den Tavern is now closed.
Several businesses are located in this historic building with its interesting cut stone. The Fox's Den Tavern is now closed.
Here's a wider shot but the same view of Washington Street.  You can get an idea of the contrasting architectural styles in Middleburg.
Here's a wider shot but the same view of Washington Street. You can get an idea of the contrasting architectural styles in Middleburg.
Across the street, one of the buildings is occupied by a bank while the other is occupied by an ice cream shop.
Across the street, one of the buildings is occupied by a bank while the other is occupied by an ice cream shop.
Just next door as you continue heading west along Washington Street is a supermarket with (unfortunately) a large suburban-style parking lot.
Just next door as you continue heading west along Washington Street is a supermarket with (unfortunately) a large suburban-style parking lot.
Along one of the sidestreets, North Pendleton Street, just across from that large parking lot, are some more businesses housed in historic buildings.
Along one of the sidestreets, North Pendleton Street, just across from that large parking lot, are some more businesses housed in historic buildings.
Antique dealers make their home inside this Antique Emporium located inside an historic stone structure on Washington Street in Middleburg.
Antique dealers make their home inside this Antique Emporium located inside an historic stone structure on Washington Street in Middleburg.
Along Washington Street are more restaurants and boutiques.
Along Washington Street are more restaurants and boutiques.
Middleburg's Post Office is located right on Washington Street.
Middleburg's Post Office is located right on Washington Street.
You can find an interior design studio or eat at an outdoor cafe or walk your dog along Washington Street in Middleburg, Virginia.
You can find an interior design studio or eat at an outdoor cafe or walk your dog along Washington Street in Middleburg, Virginia.
This shop has added quite a bit of color to its historic frontage.
This shop has added quite a bit of color to its historic frontage.
This house has been transformed into a studio, and its front yard is now a courtyard with stone-covered patio.
This house has been transformed into a studio, and its front yard is now a courtyard with stone-covered patio.
A view looking east along Washington Street, including folks enjoying eating outdoors in front of an historic tavern.
A view looking east along Washington Street, including folks enjoying eating outdoors in front of an historic tavern.
This place looks like it may have once been a garage, but as a Cidery and Distillery, it looks like it's definitely worth a visit.
This place looks like it may have once been a garage, but as a Cidery and Distillery, it looks like it's definitely worth a visit.
As we get closer to the west end of the town's commercial district, we reach the Middleburg Community Center.
As we get closer to the west end of the town's commercial district, we reach the Middleburg Community Center.
And our tour comes to an end on the western edge of Washington Street.  On the top of the hill is the National Sporting Library & Museum.
And our tour comes to an end on the western edge of Washington Street. On the top of the hill is the National Sporting Library & Museum.

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