Milford to Windham: Road Trip Guide & Distance

How far is Milford from Windham?

The distance from Milford to Windham is 44.8 miles (72.1 km) as the crow flies. Windham is located SW of Milford. By car, the driving distance is approximately 58.2 miles, taking about 1h 10min. A direct flight would take roughly 35min. Both are located in United States — Milford in Massachusetts and Windham in Connecticut.

This is a quick and easy drive, perfect for a day trip or weekend getaway. You can easily make the round trip in a single day. 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 Milford and Windham. 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.