Cana Vineyards
Credit : Miles Partnership / Neal Alfano Photography
The Red Fox Inn & Tavern
Credit : Visit Loudoun
Historic Middleburg
Credit : Visit Loudoun , Neal Alfano Photography ,
Miles Partnership
A stroll along the brick-paved sidewalks of Washington Street , past the Red Fox Inn , past Cuppa Giddy Up coffee shop , past Hunt Country Realty , drives home the notion that in Middleburg , equestrian life rules . Pedestrians in jodhpurs and riding boots amble by , and a passing SUV sports a custom “ Horse Enthusiast ” license plate . In the rolling countryside beyond the town are acres of impeccably groomed lawns bordered by whitewashed or stacked stone fences . Winding gravel driveways lead to sprawling estates with evocative names . Fox Chase . Wind Fields . Hickory Tree .
Located 45 miles west of Washington , D . C . ( 20 miles from Dulles International Airport and 48 miles from Reagan ), this town of only 700 residents packs a lot into a compact space . It ’ s the site of two high-profile horse races in spring and fall . It boasts a lively arts scene , including an annual film festival that draws high-watt celebrities . And vineyards and wineries have taken root throughout the region .
What you won ’ t find here are big-box stores and fast-food outlets .
“ The vibe here is , ‘ I don ’ t want to go to the mall ,’” says Susan Byrne , who left the bustle of Washington , D . C ., to open a namesake art gallery in 1995 . “ People here love the outdoors . They aren ’ t afraid of mud or manure .”
Four local foxhunting clubs mean there ’ s a hunt underway on most days . One of them , the Piedmont Fox Hounds , founded in 1840 , is the nation ’ s oldest . The country ’ s first horse show , the Upperville Colt & Horse Show ( eight miles west of Middleburg ), has been going strong since 1853 .
Its hunt country image grew in the early 20th century when fox hunters from Boston and New York sought greener pastures to pursue their sport as development consumed hunt territory up north .
High-profile residents have included John F . Kennedy and his family . Three weeks before JFK ’ s assassination , work was completed on the family ’ s family home . In the ‘ 70s , Elizabeth Taylor was a fixture in town during her marriage to Sen . John Warner , owner of a nearby farm . Philanthropist and art collector Paul Mellon was a longtime area resident .
The town has long attracted well-heeled retirees , affectionately referred to as “ spooks ” ( ex-CIA types ) and “ kooks ” ( eccentrics ). But some locals , like Punkin Lee , a Middleburg native and longtime operator of Journeymen Saddlers tack shop , reject the notion that her town is a haven for the wealthy .
“ Middleburg gets a bad rap for being a rich person ’ s place . It ’ s a real community that everyone participates in ,” she declares . “ Often , you don ’ t even know what ( a resident ) did until you read their obit .”
If the place ’ s sporting life and natural beauty turn heads , so does its long history . Middleburg was established by a Revolutionary War officer in 1787 . Its name is derived from its midpoint location for stagecoaches between Alexandria and Winchester , VA .
Strict historical review strictures limit downtown development and 160 buildings rate official historic status . Notable among them is the Red Fox Inn & Tavern . Established in 1728 , it claims fame as the country ’ s oldest continuously run inn and tavern . George Washington stopped here . Elizabeth Taylor was a Tap Room regular . Jackie O . slept here . ( A framed
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