Waynesboro to Winchester, Kentucky: Road Trip Guide & Distance

How far is Waynesboro from Winchester, Kentucky?

The distance from Waynesboro to Winchester, Kentucky is 287.9 miles (463.4 km) as the crow flies. Winchester, Kentucky is located W of Waynesboro. By car, the driving distance is approximately 360 miles, taking about 7h 14min. A direct flight would take roughly 1h 5min. Both are located in United States — Waynesboro in Virginia and Winchester, Kentucky in Kentucky.

For a drive of this length, it's recommended to plan at least one quick rest stop to stretch your legs and grab a coffee. 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 Waynesboro 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.