The short Keuka Outlet Trail, located in western New York State, was once a short branch of the New York Central System (NYC). The railroad dated to the late 1870s and at that time was known by another name. Soon after it was completed, the line became another of the Fall Brook Coal Company’s network of railroads before it was acquired by the NYC. However, even before trains, the right-of-way was used as the Crooked Lake Canal, offering water transportation between Seneca Lake and Keuka Lake. Despite being such a short branch, which reached nearby Penn Yan, the line survived through the NYC era and into the days of the ill-fated Penn Central. It was finally abandoned after flooding rains in 1972 severely damaged the right-of-way.

The original corridor, Crooked Lake Canal, was completed in 1833 and featured 28 locks along its route between the lakes. It was used for more than 40 years until autumn 1877 when railroad officials with the Syracuse, Geneva & Corning Railroad (SG&C) requested purchasing the canal’s towpath right-of-way to build the Penn Yan & New York Railroad (PY&NY). Despite its long name, the PY&NY would run only 6.43 miles from a connection with the SG&C at Dresden to Penn Yan. The SG&C, completed in 1877 between Corning and Geneva, was one of several railroads either constructed or purchased by John Magee that dated to the early 1850s. His initial interest in rail transportation was for moving coal from his mines in northern Pennsylvania and southwestern New York. However, as the 19th century progressed, his network expanded to the point that by the late 1880s, Magee owned a system of railroads (controlled through his Fall Brook Coal Company) running nearly 260 miles from Lyons, New York, to Williamsport, Pennsylvania, including several branches.

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On November 8, 1877, the right-of-way of the Crooked Lake Canal was sold to the PY&NY for $3,333. Not until the late fall of 1883 did efforts get seriously underway to begin constructing the railroad. By late May 1885, most of the PY&NY had been completed and it officially opened on August 3 of that year. Rail service on the SG&C’s new Penn Yan Branch grew quickly, and it was soon running three trains per day along the line, carrying everything from passengers (7,000 after just 30 days following its opening) to general freight. Within a year, freight volume had expanded to roughly 400 tons daily, which was mostly agricultural such as grapes and flour.

Overall, the SG&C was quite pleased with its new line, which while short, proved to be profitable. During summer 1888, the Penn Yan Branch opened a dock along Lake Keuka to interchange freight traffic with barges in service at the time. During 1892, Magee divested his railroads from his coal operations, creating the Fall Brook Railway. Under this arrangement, the Fall Brook took over what was formerly the Corning, Cowanesque & Antrim (running between Corning, Blossburg, Harrison, and Antrim) and leased all other properties, including the SG&C (Geneva, Corning, and Penn Yan), Geneva & Lyons (connecting its namesake towns and interchanging with the New York Central & Hudson River at Lyons), and the Pine Creek Railway (from Stokesdale to Williamsport, PA).

On May 1, 1899, the NYC&HR leased the entire Fall Brook Railway system and outright purchased it a decade later in 1909, becoming the Geneva, Corning & Southern Railroad. In 1914, when the NYC&HR became simply the New York Central System through the reorganization and consolidation of several subsidiary systems, the GC&S became known as its Fall Brook Division. These secondary lines not only reached Williamsport, but also stretched throughout central and western parts of Pennsylvania, tapping many other coal mines along the way. Over the years, traffic along the Penn Yan Branch slowly dried up as barges stopped interchanging and businesses closed. Passenger service along the line ended after 1953, which was then only a mixed train (a consist carrying both freight and passengers) offering tri-weekly service. In 1968, the NYC merged with the Pennsylvania Railroad to form the massive Penn Central system.

For four years following this merger, the Penn Yan Branch ran local freight trains until heavy flooding caused by Hurricane Agnes during June 1972 damaged the line to such an extent that the railroad did not feel justified in repairing the washouts given the little remaining freight.

Railroad attractions near the Keuka Outlet Trail include the Utica Union Station in Utica (a museum inside the city’s restored depot); Salamanca Rail Museum in Salamanca; Roscoe O&W Railway Museum in Roscoe; Rochester & Genesee Valley Railroad Museum in Rush; New York Museum of Transportation in West Henrietta; Medina Railroad Museum in Medina; Martisco Station Museum in Marcellus; Finger Lakes Railway in Geneva; Central Square Station Museum in Central Square (a depot museum inside the restored New York, Ontario & Western facility); and the Arcade & Attica Railroad in Arcade.