The Middleburg-to-the-Plains Loop in Virginia, an excellent day ride, is a quick jaunt through the Northern Virginia farmland and vineyards with mountain views on the horizon. The entire loop is only 25 miles, but the ride is relaxing, beautiful, and full of small-town Virginia charm plus a dose of Civil War history. It is also the home of many of Virginia’s most renowned horse farms.
Route of The Middleburg-to-The-Plains Loop
Head west from the historic Red Fox Inn in Middleburg, VA, on US Highway 50 for a few blocks, then turn left on Route 626, also known as South Halfway Road or The Plains Road. You will be traveling seven miles toward the town of The Plains.
Upon driving through The Plains, turn right (west) onto US Highway 55. After about 4.5 miles, as you approach the town of Marshall, turn right onto Route 710, Rectortown Road. After about six miles, turn right again onto Route 713, Atoka Road.
After about eight miles, you’ll reach Route 50. Turn right again, and US 50 will return you to The Red Fox Inn after six miles.
Points of Interest Along the Loop
In addition to the magnificent scenery, you’ll find a few points of interest along the way on The Middleburg-to-The-Plains Loop.
- Only a few minutes after you begin, at 1708 Halfway Road, on the right you’ll see the home of Gen. William “Billy” Mitchell, called Boxwood Farm. A National Historic Landmark, it’s a private residence not open to the public. Mitchell, a distinguished WWI aviator, was the first American Army first aviator to be decorated and the first to cross enemy lines. In the 1920s, as Assistant Chief of the Air Service, Mitchell worked to overhaul America’s national defense structure, buying new bombers and dirigibles for the U.S. Air Service, and pushed for the development of a U.S. airways system.
- Immediately south on Route 626, you’ll see signs for the Boxwood Estate Winery, open Wednesdays-Sundays 11 a.m. to 6 p.m. at 2042 Burrland Lane. This outstanding winery is owned by John Kent Cooke, former owner of the NFL Washington Redskins. Cooke’s wines are in the French Bordeaux tradition. Stop and taste some Cabernet Sauvignon, Merlot, Cabernet Franc, and Sauvignon Blanc.
- In The Plains, if you’re hungry, try out the food at the Front Porch Market & Grill, The Rail Stop, or Girasole. You’ll also find antique shops, coffee shops, and a tea room.
- After leaving The Plains, the area from Marshall through Rectortown and north is full of Civil War history. As you drive north on Atoka Road, the intersection with Five Points Road and Old Carter’s Mill Road is the site of a New Year’s Day skirmish in 1864, when 80 Union Soldier’s of Cole’s Maryland Cavalry happened to meet the Confederate Mosby’s Rangers. When the Rangers wounded the Union commander, the Union cavalrymen dispersed and fled, but 35 of them were captured and sent to Confederate POW camps.
- As you return to The Red Fox Inn & Tavern in Middleburg, you’ll note the splendid historical building, dating to 1728, originally owned by George Washington’s cousin Joseph Chinn. For centuries, it’s been a gathering place for politicians and celebrities alike. Stop in for a meal, a tavern drink, or a night in this historic roadhouse.
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