The Cady Way Trail is a 6.5-mile (10.5 km) rail trail in the Orlando, Florida area opened in 1994. It is partly owned by the Orlando Department of Families, Parks and Recreation and partly by Orange County Parks and Recreation. The project was awarded a $1,750,000 Transportation Enhancement grant by the Federal Highway Administration and the Florida Department of Transportation, and a $483,000 grant from the Florida Department of Environmental Protection.
The Cady Way Trail was constructed along the abandoned roadbed of the East Florida & Atlantic Railroad, which ran to the Naval Training Center Orlando. Its south end is at Orlando Fashion Square, and its north end is at Hall Road at Aloma Avenue in Goldenrod at the Seminole County line. It continues northeast approximately 2 miles (3.2 km) as the Cross Seminole Trail. Departing south from Hall Road, the trail passes Goldenrod Park, crosses State Road 436 via a bridge opened in November 2006, then passes Cady Way Park, Ward Park, Brookshire Elementary School, Winter Park High School, the former Naval Training Center Orlando (now the community of Baldwin Park) and the Winter Pines Golf Club. Part of the trail also passes through the city of Winter Park.
The second phase of construction connected the Cady Way Trail with the Cross Seminole Trail and Little Econ Greenway.