In 1878, Simonds joined Jenney's architectural practice in Chicago. His first project was Graceland Cemetery where he learned naturalistic English-style landscape design. Through Jenney's tutelage, he learned how to use native plants in landscape design, an unusual practice at the time. 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.[3] In 1880, Graceland was increasingly deferring to Simonds about the amount of work and money required to develop the property's eastern section before Jenney which led to ending Jenney's involvement in the project. This led to Simonds establishing the firm of Holabird & Simonds to carry out the work.[3][4] In 1881, Martin Roche, who had also worked in Jenney's office, joined them as a third partner. In 1883, Simonds left the firm to concentrate solely to become the superintendent at Graceland.[3] His work at Graceland led him to be called the "dean of cemetery design."[1] In 1897, he left his position at Graceland but continued to be their landscape consultant for the rest of his career.[3][1] In 1900, the cemetery was awarded a silver medal at the Exposition Universelle in Paris for its landscape and later a Medal of Honor by the Architectural League of New York in 1925.[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. Simonds used a natural ravine to boarder the meadow created for the purpose. A scenic drive was incorporated into the plan which showcased natural vistas and brick and stone officers' housing. The effect of the plan was lauded as picturesque and charming.[1]
In 1903, Simonds formed Simonds and Company and was awarded the redesign and extension of Chicago's Lincoln Park with Bryan Lathrop and Francis T. Simmons. The plan was to double the parks 275 acres by extending it into Lake Michigan and later extended it north approximately 1,000 acres. To update the older sections, he incorporated winding pathways and facilities so as not to compromise the landscape. He relied on natural topography to create naturalistic "rooms" and scenic meadow vistas.[1] He also designed golf courses, Belle Meade, city parks, town plans, universities including Iowa State and the University of Maryland, residences, and private estates around the country.[3][1]
In 1920, Simonds authored Landscape Gardening.[6] In the book, he lays out his approach to landscape design which looks to nature to inform the design. This included the use of native plants, the use of greenways, and warning of urban sprawl.[7] He also founded the Chair of Landscape Design at the University of Michigan (U of M). 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.
Simonds died November 20, 1931, after an extended illness in Chicago.[2]
Washington Park, Bounded by Fayette Ave., Williams Blvd., Walnut St., MacArthur Blvd., S. Grand Ave. and Chatham Rd. Springfield, IL Simonds, Ossian Cole, NRHP-listed[9]
Hill House, Mill Neck, NY, Residence of Anton Gysberti Hodenpyl
Pier Cove Ravine, a nature reserve on the shores of Lake Michigan, south of Saugatuck, MI and west of Fennville, MI, at approximately 2308 Lakeshore Dr, Fennville, MI 49408[10]
Mara Geldbloom, Ossian Simonds: Prairie Spirit in Landscape Gardening, in: The Prairie School Review 12, 2 (1975).
Robert E. Grese, Ossian Cole Simonds, in: William H. Tishler (Ed.), American Landscape Architecture. Designers and Places, Washington, D. C., Preservation Press 1989.