Just as in the 1700s, Rappahannock County has an economy that is agriculturally based and a landscape that is dotted with small villages. Villages typically began as frontier posts or crossroads and today provide retail services, meeting places, post offices and church activities for residents. Present-day Amissville, Castleton, Chester Gap, Flint Hill, Sperryville, and Woodville are the most recognized villages and the Town of Washington is the county seat.
Amissville is the only village to still hold an annual carnival. The proceeds help fund the fire and rescue department, an all-volunteer organization. Amissville also has the county’s first cidery-meadery.
Castleton is primarily country homes and farmland with the exception of the Castleton Festival. This musical venue, founded by the late conductor Loren Maazel, offers opera and other musical performances.
Chester Gap is the most remote village and the coolest, weather-wise. You can literally have your head in the clouds here before the morning fog lifts. Sitting atop the mountain off Rt. 522 en route to Front Royal, it offers panoramic views of the valleys below that seemingly stretch forever.
Flint Hill offers outstanding hospitality with three popular restaurants and has an art studio offering classes in various art forms. When Shenandoah National Park was created, some of the mountain residents were relocated to Flint Hill on the aptly named Resettlement Road. During the Civil War, Mosby’s Rangers frequented Flint Hill and nearby Huntly. Area markers tell the story of Chaplain Willis of the Rangers who traded his own life to save a fellow soldier; he was hanged. Willis Chapel in Huntly was built in his memory.
Sperryville, a gateway to Shenandoah National Park, flourishes with six restaurants, a bar, grocery, breweries, distillery and nine-hole golf course. The fire and rescue unit sponsors the county’s July 4 celebration and is the beneficiary of funds raised. The town also hosts SperryFest, an annual street festival of art, food and wine that celebrated its second year in 2019.
Town of Washington. Legend has it that the Town of Washington was surveyed and plotted by George Washington in 1749 and established as a town in 1796. It is fondly called “Little Washington” to distinguish it from nearby Washington, D.C. It is the county seat and site of the courthouse and county offices. It also lays claim to unique shops offering an array of specialty items.
Woodville is a smaller, quieter village with a beautiful old cemetery, large farms, horses and cattle and spectacular mountain views. The village is the birthplace of John Jackson, a grave digger who became internationally famous as a blues guitarist and singer. The first John Jackson Piedmont Blues Festival was held on Eldon Farms in September, 2019.