Upperville, VA

In 1797 this bucolic setting on the Ashby Gap Turnpike (Rt. 50) was known as Carr Town, for founder Joseph Carr. An Act of Assembly in 1819 put on the map the 30 acres known as Upperville. It is the home of the Upperville Colt & Horse Show – the oldest existing show in America, and one of the best – with the $150,000 Budweiser Jumper Classic scheduled for the final Sunday of the weeklong competition.