West Orange Trail
A town built around a trail
The West Orange Trail's 22 paved miles run straight down Plant Street, and Winter Garden is a state-designated Trail Town because of it. Where to get on, park, and rent.
HomeWest Orange Trail
The local angle
The trail is the main street
The West Orange Trail runs from the Lake County line through Oakland, straight down the middle of downtown Winter Garden, and on toward Apopka — about 22 paved miles built on an old rail corridor. Downtown, the trail literally shares Plant Street with the shops and restaurants, which is why Saturday mornings here look like a cycling event that never quite ends.
The Winter Garden Station trailhead sits downtown with parking and rentals nearby; Chapin Station and Killarney Station bracket the route for longer rides.