In 1848, Charles Shepard and his family were released from slavery when their former enslaver, Sarah Edmonds of Fauquier County, Virginia, died and freed them in her will.

[2][3] In 1906 the women of Pleasant Ridge formed the Autumn Leaf Society, a philanthropic group that organized community dances and celebrations, including an annual barbecue each August.

[2] In 1895, Pleasant Ridge's African American residents owned nearly 700 acres of farmland, but in the 20th century the population began to decline.

Ollie Green Lewis, a descendant of the Shepard family and the last African-American resident, died at Pleasant Ridge in February 1959.

[2][3] In the 21st century, only the Pleasant Ridge Cemetery remains at the site with a historical marker erected by the Wisconsin chapter of the Daughters of the American Revolution in 1994.