The Upperville Colt & Horse Show, conceived by Colonel Richard Henry Dulany and first held in 1853, remains the oldest such event in America.

Near Upperville, Californian Henry T. Oxnard built a horse breeding operation in 1903 that he named Blue Ridge Farm.

Over the years, others who came to live in the area included heiress Isabel Dodge Sloane, who built the highly successful Brookmeade Stud, Llangollen estate where Liz Whitney Tippett lived for nearly six decades, Bertram and Diana Firestone's Newstead Farm, Sandy Lerner's,[3] and the very prestigious Rokeby Farm of Paul Mellon.

It was Mellon who donated the money to build Trinity Episcopal Church in 1960, which is at the center of the small community's social activities.

Since 1960, the Hunt Country Stable Tour has raised money for the outreach programs of Trinity Episcopal Church.