The New York and Greenwood Lake Railroad was controlled by the New York & Oswego Midland and was intended to link the Midland Route to the Hudson River and New York City. The line was poorly built and had cost much more than planned. The line between Greenwood Lake and Middletown, New York would have required a tunnel under Sugar Loaf Mountain and was never built. The collapse of the NY&OM also doomed the NY&GL to bankruptcy.

The line ran from the Erie at Jersey City through Montclair and on to Greenwood Lake at the New York State line at Sterling Forest. There were three branches: the Orange Branch to West Orange, the Caldwell Branch to Essex Fells and a connection with the Morristown & Erie, and the Ringwood Branch to Ringwood. After the Midland Route dream was dead the line reorganized as an independent line under the control of the great iron industry families of Hewitt and Cooper. The line provided steamboat service with several ships to the hotels and docks on Greenwood Lake via the Greenwood Lakes Transportation Company.

Eventually the line was absorbed into the Erie. Passenger service to the Lake ended in 1935. Commuter service continued to Wanaque-Midvale until 1966. Today everything north of the connection with the NYS&W at Pompton Junction and all three branches with the exception of the first half of the Orange branch are gone. The line spent most of its life as branch of the Erie and Erie Lackawanna, today the part south of Wayne is part of NJ Transit's Booton line and north of there is the NYS&W's Pompton Branch.