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 world-class dining and bustling shops. 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 hosts an annual carnival the proceeds of which help fund the local, all-volunteer fire and rescue department. Amissville also was home to the county’s first cidery-meadery.
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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.
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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, a variety of shops, and an instructional art studio. 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. 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 a nine-hole golf course. The town also hosts SperryFest, an annual street festival of art, food, and wine.
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Town of Washington. Town of Washington. Legend has it that the Town of Washington was surveyed and plotted by George Washington before being established as a town in 1796. It is fondly called “Little Washington” to distinguish it from nearby Washington, D.C. In addition to being the County Seat, it is home to several shops, art galleries, B&Bs, and restaurants, including the world-famous Michelin Three-Star restaurant, The Inn at Little Washington.
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Woodville is a smaller, quieter village with a beautiful old cemetery, large farms, and spectacular mountain views. The village is the birthplace of John Jackson, a local gravedigger who became internationally famous as a blues guitarist and singer. The first John Jackson Piedmont Blues Festival was held in Woodville in 2019.