Running the Cady Way Trail in Orlando
Adventure Destination

Running the Cady Way Trail in Orlando

Explore the Cady Way Trail in Orlando, a 7.2-mile easy route with scenic urban views. Ideal for trail running and biking, the trail is accessible year-round with best visits in spring and fall to avoid summer crowds. Perfect for beginners seeking a quick, accessible run.

Trail Running6.0/10Easy
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Category

Trail Running

Typical Duration

2-4 hours

Difficulty

Easy

About This Adventure Destination

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.

Editorial Assessment

The Cady Way Trail in Orlando offers a pleasant outdoor adventure experience with well-maintained pathways and scenic views. However, it lacks the unique natural geological features that distinguish the most iconic outdoor destinations worldwide.

Running the Cady Way Trail in Orlando

Adventure Guide to Running the Cady Way Trail in Orlando

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1. Start at the Fashion Square Mall Trailhead

  • Overview: 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.
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Local Insights

  • Overview: 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.
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Visitor Tips

  • Details: **Best times to visit**: Early mornings (to avoid crowds and heat) or evenings.
  • Details: **What to bring**: Running shoes, sunscreen, water, and a basic first aid kit.
  • Details: **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.

Reviews

L
Larry Wilsona month ago

Incredible experience! The views and natural scenery at Running the Cady Way Trail in Orlando are unforgettable. Well marked trails and a fantastic outdoor getaway.

P
Peter M.3 months ago

Clean trails with great directions. Once you arrive, there are multiple scenic vantage points to explore. Highly recommend visiting early in the morning.

D
David Pestana6 months ago

One of my favorite destinations in the region. Sunset here transitions into an unforgettable evening with shifting light on the landscape.

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