Lexington, Kentucky to Winchester, Virginia: Road Trip Guide & Distance

How far is Lexington, Kentucky from Winchester, Virginia?

The distance from Lexington, Kentucky to Winchester, Virginia is 351.3 miles (565.3 km) as the crow flies. Winchester, Virginia is located ENE of Lexington, Kentucky. By car, the driving distance is approximately 421.5 miles, taking about 8h 29min. A direct flight would take roughly 1h 12min. Both are located in United States — Lexington, Kentucky in Kentucky and Winchester, Virginia in Virginia.

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. Heading East means you'll be driving into the sunrise if you start early. Keep your windshield clean for the best visibility.

Coordinates come from public place data for Lexington, Kentucky and Winchester, Virginia. 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.