The Cady Way Trail is a 3.8-mile (6.1 km) long rail trail in the Orlando, Florida area. It is partly owned by the City of Orlando Parks Division. Part of the trail also passes through the city of Winter Park, as well as unincorporated areas of Orange County.
It is built along an abandoned East Florida and Atlantic Railroad (later Seaboard Air Line Railway) corridor which ran to the Orlando Naval Training Center (now Baldwin Park).
Its south end is at Orlando Fashion Square Mall, and its north end is at Hall Road at Aloma Avenue in Goldenrod, at the Seminole County line. It continues northeast approximately a further 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 Orlando Naval Training Center and Winter Pines Golf Club.