Kingsport to Winchester, Kentucky: Road Trip Guide & Distance

How far is Kingsport from Winchester, Kentucky?

The distance from Kingsport to Winchester, Kentucky is 133.5 miles (214.9 km) as the crow flies. Winchester, Kentucky is located NW of Kingsport. By car, the driving distance is approximately 166.9 miles, taking about 3h 21min. A direct flight would take roughly 46min. Both are located in United States — Kingsport in Tennessee 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. Given the short distance, driving or taking a train is often faster and more convenient than dealing with airport security and flight boarding times.

Coordinates come from public place data for Kingsport 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.