Charlottesville to Winchester, Kentucky: Road Trip Guide & Distance

How far is Charlottesville from Winchester, Kentucky?

The distance from Charlottesville to Winchester, Kentucky is 310.4 miles (499.6 km) as the crow flies. Winchester, Kentucky is located W of Charlottesville. By car, the driving distance is approximately 388 miles, taking about 7h 48min. A direct flight would take roughly 1h 7min. Both are located in United States — Charlottesville in Virginia and Winchester, Kentucky in Kentucky.

This is a solid day of driving. Be sure to take breaks every 2-3 hours to avoid driver fatigue, and plan your meals ahead of time. Since you'll be heading mostly West, pack a good pair of sunglasses if you plan to drive during the late afternoon to avoid the harsh sun glare.

Coordinates come from public place data for Charlottesville and Winchester, Kentucky. The driving distance is estimated from straight-line distance with a road-factor model, so confirm the route in your navigation app. Fuel, flight, bus, and train values are planning estimates and can change by date, provider, road closures, and border rules.