A 6.5-mile (10.5 km) asphalt rail trail, the path follows a railway corridor that previously connected residential and recreational areas of Winter Park, Florida with Orlando Fashion Square and neighborhoods in Orange County, Florida.

Along its length, the trail has sheltered benches, trash bins, water fountains, and numbered markers.

A second phase of expanding the trail was planned, and has already received one US$1.75 million grant from Federal Highway Administration and Florida Department of Transportation, and another from the Florida Department of Environmental Protection for $483,000.

[1] In April 2012, two Winter Park High School students—Nick Presha and Jeremy Stewart—were executed on the Cady Way Trail.

Jesse Davis and Hector Rodriguez (both born in 1981 or 1982) were found guilty of the murders, and sentenced to life imprisonment.