Best events in

Upperville

Events and things to do in Upperville, VA centre on historic equestrian grounds and rolling hunt country pastures. The Route 50 corridor brings together preserved stone architecture, casual country pubs, and lively community gatherings. Local routines flow naturally from daytime agricultural pursuits into relaxed evening tastings across estate vineyards.

• Moving through the Village Center along Route 50 reveals preserved 18th-century stone structures, historic churches, and casual community hubs like Hunter's Head Tavern.
• The sprawling Upperville Hunt Country provides scenic backdrops for outdoor recreational pursuits and historic agricultural grounds at Grafton & Salem Show Grounds.
• Estate venues such as Slater Run Vineyards host recurring acoustic music sessions and seasonal food gatherings on expansive country lawns.