From Orange, travel south on Route 15 toward Gordonsville. There are views of Orange County, but this is Madison Country. Land in the vicinity was part of the Madison family’s Montpelier patent of 1723. Mayhurst, built in the 1850s was the home of John Willis, great grandnephew of James Madison. Gordonsville grew rapidly with the arrival of two railroads in the 1840s. In 1862, Stonewall Jackson had his headquarters at the old Gordon Tavern. The Gordonsville Hospital, which occupied the Exchange Hotel, treated more than 70,000 soldiers and is now the Exchange Hotel Civil War Museum.
Leaving Gordonsville, travel north on route 231, the old Blue Ridge Parkway through rolling hills with mountain views and historic estates. North of Route 20, cross the Rapidan River into Madison County. At the junction with Route 230, you can continue north toward Madison or enjoy an interlude of picnicking and a hike along the Rapidan River in Shenandoah National Park.
Follow Route 662 six miles through striking scenery to Route 231 leading into Madison. The county courthouse is an architectural marvel. Route 231 north from Madison to Sperryville is a beautiful scenic drive with views of the mountains in Shenandoah National Park. Route 231 ends at Route 522. Turn right to return to Culpeper.