The New York & Oswego Midland Railroad was born out of a necessity to connect the port of Oswego (on Lake Ontario) with the great port of New York City by the most direct route. It was conceived as an “airline” railroad – and rival to the New York Central Railroad. Its route, however, ended up meandering from one small community to the next so that forever after its operation was of minor competitive harm to the Central Road. This was the railroad that was inherited by the New York, Ontario & Western Railway when a group of investors purchased the Midland at a foreclosure sale in 1879. For seventy-eight years, the O&W could never shake itself from the inferior route of its predecessor, yet, along the way, residents of its online communities fell in love with its quintessential charm. The O&W was their railroad and they supported it as best they could. When one resident was asked why he traveled to New York City on the O&W rather than the speedier New York Central, he responded, “I wouldn’t think of going any other way. This is my railroad.” It was because of its second-rate status, its desire to succeed, and its communities hoping for its success that it is so fondly remembered today. This is the story of the O&W’s trials, tribulations, and success on its lines north of Sidney, New York. Because of its dedication to service during life it is still well remembered after nearly fifty years of death. The purpose of Remembering the New York Ontario & Western Railway: Oswego to Sidney & Branches is to perpetuate the memory of the railroad whose great success was endearing itself to the communities it served. Memories are made of such things; the remembrances herein help to keep the New York, Ontario & Western Railway alive–if only in our minds.