Simonds was born in Grand Rapids, Michigan, on November 11, 1855, where he developed a love of nature through his explorations of its woods.

[1][2] From 1874 to 1878, he studied civil engineering at the University of Michigan and, briefly, architecture with William Le Baron Jenney.

He studied local woods, hydrology, and topography leading him to be credited with the creation of the Prairie Style along with Jens Jensen, and Walter Burley Griffin.

[5] In 1888, Ossian Cole Simonds' first project after Graceland was to create a site plan for Fort Sheridan which was to include a parade ground for drills.

A scenic drive was incorporated into the plan which showcased natural vistas and brick and stone officers' housing.

In 1929, he was honored with a master's of arts from U of M.[8] In 1922, Simonds designed the grounds of the Morton Arboretum in Lisle, Illinois.