Running the Cady Way Trail in Orlando

The Cady Way Trail offers runners a scenic escape into nature right in the heart of Orlando, Florida. This 7.2-mile path seamlessly connects urban convenience with outdoor serenity, making it an essential running route for locals and visitors alike. Stretching between Orlando and Winter Park, the trail features a mix of paved lanes through lush greenery, suburban landscapes, and even access to popular recreational spots. Whether you’re a seasoned runner or a casual jogger, the Cady Way Trail has something for every fitness enthusiast.

Adventure Guide To Running the Cady Way Trail

Start at the Fashion Square Mall Trailhead
Located near the Orlando Fashion Square Mall, this trailhead is one of the most popular starting points. With ample parking and restroom facilities, it’s a convenient access point for runners. The trail here features wide paved paths and mild elevations perfect for a smooth warm-up or a light jog.
Cross the Cady Way Trail Bridge
Among the highlights of the trail is the iconic bridge that safely carries runners above busy State Road 436. This portion not only offers a practical crossing but also provides sweeping views of the surrounding area—particularly stunning during sunrise or sunset runs. The modern design of the bridge adds a unique touch to the experience.
Eastbrook Greenway Section
Toward the trail’s Winter Park end, runners encounter the Eastbrook Greenway, where the path winds through tree-canopied sections and peaceful residential areas. This section is especially popular among local runners for its shaded paths and tranquil ambiance, ideal for cooling off during the final leg of a route.

Local Insights

The Cady Way Trail is home to a piece of Orlando history—you’ll spot several markers identifying portions of the old railway system that the trail replaced. Also, keep an eye out for public art installations that enrich the trail’s character, including murals and sculptures along the route.

Visitor Tips

Best times to visit: Early mornings (to avoid crowds and heat) or evenings.
What to bring: Running shoes, sunscreen, water, and a basic first aid kit.
Driving directions: From downtown Orlando, head east on Colonial Drive (State Route 50) to the Fashion Square Mall; it’s about a 15-minute drive.