The New York & Oswego Midland Railroad, predecessor of the New York, Ontario & Western Railway, was the grandiose vision of Dewitt C. Littlejohn, a dynamic politician bearing an uncanny resemblance to Abraham Lincoln. His concept of a direct rail route northwest across New York State, serving virgin territory not reached by any existing line, seemed logical.

Thus in 1868 the "Midland" began building, meandering this way and that to reach the towns which had put up money for its construction. Its twisting route was built "at right angles to the mountains" requiring steep grades, high bridges and enormous fills. Construction costs far exceeded estimates, and within a month of completion the Midland was bankrupt. But it survived, and was reorganized in 1880 as the New York, Ontario & Western Railway, or the "O&W".

Shortly after the O&W was incorporated, its owners became involved in the promotion and construction of the New York, West Shore & Buffalo Railroad, a route that eventually would parallel Cornelius Vanderbuilt's New York Central & Hudson River all the way to Buffalo via Albany, NY. Naturally, the NYC&HR viewed the West Shore as a nuisance or blackmail scheme.

Complicated financial arrangements existed between the O&W and the West Shore which were detrimental to the corporate health of the former. However, this was mitigated by the West Shore's construction of a branch from its main line at Cornwall, NY, to Middletown in 1883 and by opening terminal facilities in Weehawken, on the Hudson River across from New York City, in 1884. These projects provided the O&W with a more reliable and more direct route to the metropolitan area than had been available with the NJM connection. The O&W-West Shore combination was dissolved when the latter entered bankruptcy in 1884 and was subsequently leased by the NYC. The Middletown Branch became part of the O&W, and NYC permitted O&W to continue using the West Shore between Cornwall and Weehawken.

The O&W underwent an administrative reorganization after its involvement with the West Shore came to an end. Thomas P. Fowler, a talented lawyer formerly with the NYC's legal department, became the new president. He is reputed to have said that he wondered why the O&W had been built and why, after entering bankruptcy, it hadn't been allowed to stay there. Regardless of his comment, he must have seen some potential in the line, and with the American economy in a period of expansion, he set out to make a respectable property of the NYO&W.

During Fowler's term, the railroad significantly aided in, or undertook the development of, several industries. It firmly established itself as a tourist carrier to the resort hotels and camps in the mountains of Orange, Sullivan, and Delaware counties (often referred to as the "Lower Catskills"). The road expanded its operations in the haulage of milk and dairy products and, most importantly, it became a carrier of anthracite coal by tapping the northern Wyoming Valley coal field in northeastern Pennsylvania through the railroad's most ambitious expansion program: the construction in 1889-90 of the 55-mile Scranton Division.

Although the coal business wavered in the 1920s, it remained strong into the early years of the Great Depression and it permitted the O&W to continue paying dividends. Nonetheless, petroleum fuels, natural gas and electricity were making ever greater inroads into coal markets. Coal was losing ground, but it definitely was not out. O&W handled only about four percent of the anthracite shipped out of Pennsylvania, but in the early 1930s, this one commodity still accounted for over 50 percent of the railroad's income. But this was an unhealthy situation, one of too great a reliance on one industry.

The decline of coal was not O&W's only dilemma. Economic activity as a whole in the U.S. was changing dramatically. Manufacturing activities were moving to the South, Southwest and West, and the resultant population shifts were changing the consumer markets and the rural economy upon which the early O&W and its predecessors had relied. What the OM's developers had promised the railroad would do had occurred, but it was Western railroads opening Western lands to agricultural development that better filled the promise. The decline in the importance of the small towns and cities, the expansion of the suburban industrial parks, and the population shifts to metropolitan areas or to other parts of the country were severely felt by "rural roads" such as the O&W.

On February 25, 1937, the O&W advised the holders of its Refunding Mortgage Bonds, due in 1992, that it could not pay the interest due on March 1. Two of the three railroad-owned collieries had earlier defaulted on their loans from the railroad. This, coupled with an overall decease in anthracite tonnage, reduced freight rates, increased taxes and other increased expenses caused the railroad to default on its financial obligations. As a result, O&W entered a voluntary bankruptcy from which it would not emerge. On March 29, 1957, the O&W became the first Class I railroad in the United States to fully abandon.

The extent of the abandonment was from Cornwall to Middletown to Summitville, with branches there to Kingston and to Port Jervis and Monitcello. From Summitville the line traveled west to Cadosia, where the branch to Scranton, PA, split off to the southwest. From Cadosia, the line went through Walton, with a branch to Delhi, then to Sidney and New Berlin Junction. At New Berlin Junction, the New Berlin Branch went to Edmeston and followed the valley of the Unadilla River. The Utica branch left the mainline north of Norwich NY at Randallsville and continued west to Utica and Rome. The main line continued to Oneida, then along the north side of Oneida Lake to Fulton. The O&W shared the line from Fulton into Oswego with the NYC. There is virtually no part of the O&W itself left in existence.

Oswego, NY: Within Oswego, the O&W tracks ran from Bridge Street northward, while the tracks south of Bridge Street were owned by the Rome, Watertown and Ogdensburg Railroad. This portion south of Bridge Street features a tunnel originally opened in 1876, and it became part of the New York Central Railroad in 1913.

Use of the tunnel for railroad purposes was discontinued in 1976. The tunnel had deteriorated by the 1990s, but has since been restored and incorporated, along with other local portions of the right-of-way, into the O&W Railroad Promenade and Bikeway, which was constructed in 2000-2001. The project was funded through the Federal Intermodal Surface Transportation Efficiency Act (ISTEA), the New York State Department of Transportation, Oswego County, and the City of Oswego.

The only remaining evidence of the line in Oswego is a railroad bridge over the Oswego River, the old New York Central Railroad Station at the corner of West 1st Street and West Utica Street, and the restored tunnel just south of Bridge Street. The bridge was covered in cement (presumably after the tracks and ties were removed), and now serves as the southern end of the O&W Railroad Promenade and Bikeway. The old New York Central Railroad Station is located just across the street from the southern end of the bridge, and is now Paul's Big M Food Depot. North of the bridge, the trail and bikeway continues through the restored tunnel and then along a very short stretch of the right of way up to East Schuyler Street. Immediately beyond either end of the trail, no other signs of the railroad can be found within Oswego as of 2008.