In 1868, the Port Jervis and Monticello Railroad was built. The line was leased to the New York Ontario and Western Railway (O&W). The O. & W. right of way and some old structures remain visible in the city, even though the tracks wee removed in 1957-58.
Map from: Minisink Valley Express by Gerald M. Best

Freight train on the branch.
Monticello branch train at Port Jervis.
Early engine on the branch,
O&W train at Middletown
Last days of operation,