Oakville to Winchester, Virginia: Road Trip Guide & Distance

How far is Oakville from Winchester, Virginia?

The distance from Oakville to Winchester, Virginia is 305 miles (490.8 km) as the crow flies. Winchester, Virginia is located SSE of Oakville. By car, the driving distance is approximately 381.2 miles, taking about 7h 40min. A direct flight would take roughly 1h 7min. Oakville is in Ontario, Canada, while Winchester, Virginia is in Virginia, United States.

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. Keep in mind this route crosses international borders. Don't forget your passport, and check current border crossing times and vehicle insurance requirements.

Coordinates come from public place data for Oakville 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.