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The New York, Ontario & Western, also known as the "Old Woman" or the "Old and Weary", was the first major railroad in the northeastern US to go bankrupt, in 1957. By 1976, every major railroad in the northeast had been merged into Conrail or abandoned outright. The NYO&W served as the canary in a coal mine for the railroad industry. Its reasons for failure were inherent in its construction in the 1870s, it was quite possibly a railroad that should never have been built.

The NYO&W began life as the New York & Oswego Midland, in 1865. Two prominent New York politicians of the time, DeWitt Littlejohn and Henry Low, conceived of a railroad connecting New York City with the port of Oswego on Lake Ontario. To raise money for its construction, Littlejohn and Low wrote a piece of legislation known as the Town Bonding Act. Towns and cities that bonded themselves to the railroad were rewarded with stations along the route. This strategy resulted in a roundabout route between Oswego and Middletown that bypassed every major city inbetween. Larger cities such as Syracuse, Utica, and Binghamton were already served by several other railroads, and had no interest in Midland bonds. From Middletown, the Midland obtained trackage rights to Jersey City, New Jersey, and the final leg of the journey was by ferry across the Hudson River.

The railroad entered receivership three weeks after construction was completed. However, by 1875, the milk traffic from farms in upstate New York allowed the railroad to reach a modest profitability.

In 1879, the railroad (which had cost $26,000,000 to build) was sold to a consortium including George Pullman, for $4,600,000. It was renamed the New York, Ontario & Western. The NYO&W was sold again in 1885, and put under the direction of Thomas Fowler, once a protege of Cornelius Vanderbilt. Under Fowler's leadership, the NYO&W prospered. In 1890, an extremely profitable 54-mile branch was built south from Cadosia, New York, to Scranton, Pennsylvania, to tap into the anthracite industry in northeastern Pennsylvania.

Thomas Fowler resigned from the presidency of the NYO&W in 1912. The railroad soon went into a slow decline. Times got tough in the 1930s, with the combined effects of the Great Depression and increased automobile ownership. The coal business also became less lucrative, as the Pennsylvania coal fields began to dry up, and gas and oil made inroads on the home heating business. In 1937, the NYO&W defaulted on its bond payments and declared bankruptcy.

The NYO&W was then operated by court-appointed trustees. During World War II, traffic increased and the NYO&W appeared to be headed back towards solvency. But when traffic dropped back to pre-war levels, the NYO&W was doomed. The problem was finding any type of profitable traffic. The farming industry in New York state was in decline, and most of the milk business was now handled by truck. The Great Lakes traffic had never amounted to much, and the NYO&W was unsuitable as a bridge line, because its route was so indirect and because it skipped most of the major cities in upstate New York. Passenger service was eliminated in 1953, and service was eliminated entirely in 1957.

One small stretch of NYO&W track still remains, in Middletown, New York, where the NYO&W's large brick stationhouse also still stands. It is used by Norfolk Southern to serve local industries and to connect its former Erie Southern Tier Line with the tiny Middletown & New Jersey.

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