Construction of the Skaneateles & Jordan Railroad Company started in 1836 at a cost of $1,500 dollars with plans to connect the small village of Skaneateles, NY, with the Erie Canal. It originally used wooden rails at the time due to a lack of sufficient funds to purchase iron rails; the railroad did find the money to buy iron rails in 1845. Starting in Skaneateles, at its depot on the Skaneateles Lake (at the location of present-day Sherwood Inn), it ran just five miles North to Hartlot, NY (later renamed to Skaneateles Falls, or "Skaneateles Junction" by the New York Central & Hudson River Railroad). Harlot was the home of the line's engine house and car shop, just off Fenal street (P&C now sits on the present site). The S&J had deep financial difficulties and was sold on Augest 24, 1850 - the first attempt to build a railraod had failed.

It was not until after the Civil War that the village and local industry requested that service be restored due to the expansion of plants along the Erie Canal. With roads being as primitive as they were, a new railroad, the Skaneateles Short Line Railroad, with help from the community and industries, gathered $100,000 and began reconstruction on April 18, 1866. With the help of men hired on immediately from the New York Central, total construction of the railroad was $88,877.29. The SSLR opened a steam boat operation for dinner cruises and mail boats sailed along Skaneateles Lake. The SSLR struggled for years with finances getting worse after 1930. The line lost some industries but kept plugging away. After WWII, passenger service fell to the point that the conductor was the only person on the train during its 2 daily trips from Skaneateles Junction to the town of Skaneateles proper. Abandondments took place when industries started to drop service in favor of trucks. The tracks had seen no maintenance from the 1930s to the mid 1970s. On tracks still in use, the ties and ballast had just about disintegrated and derailments were common, sometimes within 1-2 feet from where they had just rerailed a car. By 1974, Stauffer Chemical was the only operating customer on the line and to ensure its rail traffic, it purchased the line and started an immediate rehabilitation program of the line which included new ballast several thousand ties. The railroad kept its own name through the Stauffer years.

On Monday, July 13, 1981 the SSLR delivered its final shipment to Stauffer Chemical and the line was cleared later that night. Ironically, returning from its last shipment to Stauffer, the small GE 44-tonner #6 derailed at a switch. Crews tried to put the locomotive back on the track using a bar and a jack. The jack broke and was smashed like a beer can after a few hours of trying to get the engine back on the tracks. A pay loader was called in to reset the engine back on the rails and that was the end of the ill-fated 5-mile short line...

The Skaneateles Short Line served 17 industries from 1836-1981 and had a fleet of 6 steam engines, all retired by 1950, and 2 GE-Erie 44-tonners which were sold to New York State Electric & Gas in 1981. From 1831-1901 the railroad also operated the Skaneateles Steamboat & Transportation Company and operated 8 boats mixed of mail and dinner boats. The boat company still lives on and runs a dinner cruise weekly. The railroad employed 12 engineers, 9 firemen, 5 conductors, 6 brakmen, 8 management staff, and 14 yard staff.