[4] The first settlers were chiefly followers of the Public Universal Friend, a religious enthusiast born in Cumberland, Providence County, Rhode Island, who obtained a large tract for a settlement (called Jerusalem in 1789) in the present Yates County, and founded the village of Hopeton on the outlet of Keuka Lake, approximately one mile from Seneca Lake.

[4][5] It became a trading center for the agricultural county, with mills for lumber, buckwheat and other grains.

In 1921, the Penn Yan Boat Company was founded by German immigrant Charles A. Herrman.

During the late 1800s and through the mid-to-late 1900s, Penn Yan and surrounding Yates County areas were home to a large number of dairy farms, many settled by Danish immigrants and their descendants.

Since the late 20th century, Old Order Mennonite and Amish families have settled and taken over farms in the region.

The Yates County Old Order Mennonites settlement is the largest horse-and-buggy community in the state of New York.

[6] There are also several Old Order Amish settlements in adjacent Steuben and Seneca counties, which were founded starting in 1979.

[9] The Roderick M. Morrison House, Lake View Cemetery, Crooked Lake Outlet Historic District, Yates County Courthouse Park District, Sampson Theatre, United States Post Office, Charles Wagener House, and Penn Yan Historic District are listed on the National Register of Historic Places.

The Chronicle-Express is Penn Yan's weekly newspaper that provides information regarding a variety of current events and updates of local news.