Ossining to Pittsfield: Road Trip Guide & Distance

How far is Ossining from Pittsfield?

The distance from Ossining to Pittsfield is 94.4 miles (152 km) as the crow flies. Pittsfield is located NNE of Ossining. By car, the driving distance is approximately 118.1 miles, taking about 2h 23min. A direct flight would take roughly 41min. Both are located in United States — Ossining in New York and Pittsfield in Massachusetts.

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. Heading East means you'll be driving into the sunrise if you start early. Keep your windshield clean for the best visibility. 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 Ossining and Pittsfield. 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.