New Haven, Connecticut to Winchester, Virginia: Road Trip Guide & Distance

How far is New Haven, Connecticut from Winchester, Virginia?

The distance from New Haven, Connecticut to Winchester, Virginia is 312.5 miles (503 km) as the crow flies. Winchester, Virginia is located WSW of New Haven, Connecticut. By car, the driving distance is approximately 375.1 miles, taking about 7h 33min. A direct flight would take roughly 1h 8min. Both are located in United States — New Haven, Connecticut in Connecticut 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. 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 New Haven, 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.