Stamford, Connecticut to Winchester, Virginia: Road Trip Guide & Distance

How far is Stamford, Connecticut from Winchester, Virginia?

The distance from Stamford, Connecticut to Winchester, Virginia is 276.3 miles (444.6 km) as the crow flies. Winchester, Virginia is located WSW of Stamford, Connecticut. By car, the driving distance is approximately 345.4 miles, taking about 6h 57min. A direct flight would take roughly 1h 3min. Both are located in United States — Stamford, Connecticut in Connecticut and Winchester, Virginia in Virginia.

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 Stamford, Connecticut 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.