Distance - 50 miles // 80 km
Elevation - 4,500 ft. // 1400 m
Est. Time - 3 - 4.5 hours
Difficulty - Moderate to Difficult ■■
This route not only offers a perfect introduction to the peerless unpaved roads of Madison County, it also boasts a number of “greatest hits” as well. You’ll want to leave enough time to fully enjoy the bucolic scenery, so this route is best for a leisurely weekend exploration.
The adventure begins with a steep gravel climb up Gaar Mountain Rd. (Rt. 652), which becomes a fun twisty gravel descent on the other side. You’ll encounter plenty of tough little climbs, so don’t overdo it at the beginning. Whipporwill Rd. (Rt. 603) is one of the area’s true gravel gems: challenging but not frustrating, it culminates in a magnificent view of Old Rag.
A few straight gravel descents in the back half reward you with some time in the drops too. The wide-open views of the Blue Ridge Mountains, shady forests, winding creeks and sunny green fields add pleasing variety to the distinctive Piedmont landscape.
Views not to Miss: You’ll come across some fantastic views of the ridge in Aylor and on John Myers Rd (Rt. 609). Whipporwill Rd. (Rt. 603) displays an especially sublime view of Old Rag (a famous mountain and hike in the area) from top of the ridge and continues to bring smiles even as you drop down into the farmlands along the river. At the end, the long downhill straightaway on Wilderness Rd. (640) is a fun gravel blast with a wide-open view. The endless views of the mountains will ensure that you keep your camera out until you make it back to Madison.
Where to stop during the ride? The route is fairly remote and does not have direct access to store stops, so plan to bring enough food and water for the entire duration of the ride. Two optional store detours are available.Two options just off the route are the Little Country Store (5338 SFT Valley Rd, Etlan, VA) and the Boston General Store (6276 Sperryville Pike, Boston, VA)
After the Ride: There are multiple great eateries in Madison as well as a an abundance of breweries and wineries in the area to further enjoy the the beautiful area.