The Cady Way Trail is a paved multi-use rail-trail of about 7.5 miles (12 km) running from Winter Park through east Orlando, linking neighborhoods, Cady Way Pool, Showalter Field and the Orlando Urban Trail network. It starts near the Cady Way trailhead in Winter Park and continues east toward Alafaya Trail and the University area. The trail is fully paved, flat and shaded in places by live oaks, with road crossings controlled by signals and signs. It is free and open from dawn to dusk. Joggers, cyclists, dog walkers and families share the path, so keep to the right and pass with a call. There are few restrooms and no drinking water along the way, so carry water, particularly from May to September, when afternoon heat and storms are strong. The trail connects Winter Park with the Cady Way Pool, Showalter Field and Winter Park Village, so food is easy to find nearby. Visitors who prefer a longer day can link to other paved routes using the Orlando trail maps.
| Distance | 7.5-mile (12 km) paved rail-trail from Winter Park to Orlando Fashion Square area, about 5 miles (8 km) northeast of downtown Orlando |
|---|---|
| Duration | 1.5-3 hours on foot; 45-60 minutes by bike |
| Difficulty | easy |
| Trailhead | Car, bike or rideshare; the trail links to the Orlando urban trail network and SunRail stations are nearby at Winter Park; trail use is free |
| Best season | November-April; early morning in summer |
| Address | Cady Way Trailhead, 2900 Cady Way, Winter Park, FL 32792 |
Trail facts
- Trail area
- Winter Park to east Orlando
What to bring
- Water
- Sunscreen
- Helmet if cycling
- Comfortable shoes
Location
Cady Way Trailhead, 2900 Cady Way, Winter Park, FL 32792
28.5880, -81.3165 View on map
Highlights
- Paved flat 7.5-mile route through Winter Park and east Orlando
- Shade from live oaks in many sections
- Connections to Orlando urban trail routes
- Free access and easy parking at trailheads
Tips for visiting
- Carry water; few fountains exist along the path.
- Keep right and announce when passing.
- Walk or ride at sunrise in summer.
- Cross roads only at signals.
- Check Orange County trail maps for connections.
When to visit
November-April; early morning in summer; go early to avoid midday heat and afternoon storms.
Accessibility
The trail is paved, flat and generally accessible to wheelchairs and strollers, with road crossings that need care.
Visit, book or contact
Frequently asked questions
How long is the walk?
7.5-mile (12 km) paved rail-trail from Winter Park to Orlando Fashion Square area. Most visitors need 1.5-3 hours on foot; 45-60 minutes by bike.
Is there a fee?
Free.
When is the best time to go?
November-April; early morning in summer.
Is the trail suitable for strollers?
Yes, it is paved and level, though road crossings need care.