The New York Central Railroad had a short, six mile, branch between Dresden on Seneca Lake and Penn Yan on Keuka Lake. This route connected to the former Fall Brook Railway at Dresden and connected with the Pennsylvania Railroad in Penn Yan, the county seat of Yates County.
In 1814 the New York State Legislature directed a survey for a canal to connect Dresden on Seneca Lake with Penn Yan on Keuka Lake (also known as Crooked Lake). Work began on the canal in April 1831 and the Crooked Lake Canal was completed on October 10, 1833. Operations ended on the canal in 1875 and on June 4, 1887 the canal was officially abandoned.
On August 24, 1887 the Penn Yan and New York Railway was incorporated and applied to purchase the canal from the state to build a railroad. The road was completed on August 3, 1884.
On October 1, 1885 the Penn Yan and New York Railway was merged into the Syracuse Geneva and Corning Railway, which was part of the Fall Brook Coal Company. The Fall Brook was eventually merged into the New York Central Railroad which operated the line until 1972 when much of the track was washed out by Hurricane Agnes. It is currently the Keuka Lake Outlet Trail and is used for hiking, biking, and other recreational uses.
The table below lists the stations on the New York portion of the line.
| Station | Distance |
| Dresden Cascade Mills Mays Mills Seneca Mills Milo Mills Keuka Mills Penn Yan |
0.0 2.2 2.6 3.3 4.6 5.2 6.1 |