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. 2. 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. 3. 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.

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.

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.