Winchester, Kentucky to Winston-Salem: Road Trip Guide & Distance

How far is Winchester, Kentucky from Winston-Salem?

The distance from Winchester, Kentucky to Winston-Salem is 253.3 miles (407.6 km) as the crow flies. Winston-Salem is located ESE of Winchester, Kentucky. By car, the driving distance is approximately 316.6 miles, taking about 6h 22min. A direct flight would take roughly 1h 1min. Both are located in United States — Winchester, Kentucky in Kentucky and Winston-Salem in North Carolina.

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. 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 Winchester, Kentucky and Winston-Salem. 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.