Distance: 27 miles
Time: 43 minutes
Start: Middleburg
End: Middleburg
While you are still in Middleburg, you should take the opportunity to try out the local cuisine at establishments like the Upper Crust, Red Horse Tavern, or Wild Hare Cider Pub. Heading west on John S. Mosby Highway, you will come across Mt. Defiance Historic Park which was once the site of the Battle of Middleburg.
Heading southwest on Atoka Road, you will encounter plenty of farms on the side of your route including Hai Sai Barn, Merry Chase Farm, Salem Oaks Farm, and Brown Hall Farm.
The return trip as you travel eastward on Highway 55 and then turning northward on Highway 626 is largely uneventful which is perfect if you are looking for a leisurely ride. The road stays relatively straight with only a few twists and turns, but you should make sure to look out for loose gravel on the surface.