Transportation in Penn Yan was accomplished on foot or horseback through the woods until the Erie Canal opened in 1825. This event lead to plans to link Keuka Lake to Seneca Lake, which then lead to the Erie Canal. The canal, completed in 1833, was the principal means of shipping freight until the first railroad arrived in the 1850s. Railroads at both ends of the lake were served by steamboats, which operated continuously from 1835 to 1922. There were seven steamboats running in the peak year of 1895. By 1915, only one steamboat was left on the lake; they had been replaced by trucks, automobiles, and buses, such as the one shown above on Jacob (East Elm) Street in a 1916 photograph.
The Kinneys Corners siding is shown in this postcard from the early 1900s. The roof of the Bluff Point Methodist Church and Yoder Hill vineyards and orchards can be seen in the background. The electrical generator for the railway was at Brandy Bay (on Keuka Lake), which was about halfway between Penn Yan and Branchport.