The regional New York Ontario & Western Railway (O&W) operated from 1868 to 1957 and ran from Weehawken, New Jersey to Oswego on the shores of Lake Ontario, passing through the southern Catskills and Sullivan County along the way. There were also branches to Kingston, Port Jervis, Monticello, Delhi, Utica, Rome and Scranton. The railway was mainly used to transport people, coal and dairy products to and from rural communities along the line and the New York City metropolitan area.

However, after years of declining fortunes, and due to lower passenger traffic, improved automobile roads, declining coal shipments and outdated equipment, the O&W went bankrupt and liquidated its assets in 1957. The O&W railway was the first Class I railroad in the United States to be fully abandoned.

The red caboose located off exit 96 of Route 17 serves as a town landmark and the unofficial entrance to the beautiful hamlet of Livingston Manor, New York. The car originally served as an Erie Railroad caboose, but was later repainted with the logo of the N.Y. O. & W. when it was moved to Livingston Manor.

The caboose was purchased in 1984 by the Livingston Manor Chamber of Commerce to serve as an information kiosk for travelers visiting the hamlet. For a short time, it was staffed with an attendant to answer questions about the area. There were plans to expand the site into a full rest stop, but those plans never materialized due a number of issues.

The Red CabooseThe red caboose located off exit 96 of Route 17 serves as a town landmark and the unofficial entrance to the beautiful hamlet of Livingston Manor, New York. The car originally served as an Erie Railroad caboose, but was later repainted with the logo of the N.Y. O.&W. when it was moved to Livingston Manor.

N. Y. O. & W. #1444 Livingston ManorThe red caboose located off exit 96 of Route 17 serves as a town landmark and the unofficial entrance to the beautiful hamlet of Livingston Manor, New York. The car originally served as an Erie Railroad caboose, but was later repainted with the logo of the N.Y. O.&W. when it was moved to Livingston Manor.