Cady Way Trail


Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 30,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Cady Way Trail Facts

States: Florida
Counties: Orange
Length: 6.5 miles
Trail end points: Aloma Ave. and Howell Branch Road/Hall Road (Winter Park) and Orlando (Fashion Square Mall, Herndon Ave)
Trail surfaces: Asphalt
Trail category: Rail-Trail
ID: 6015490
Trail activities: Bike, Inline Skating, Wheelchair Accessible, Walking

With Unlimited:

  • Export to My Trail Guide
  • Create Guidebook
  • Download GPX
  • Download Offline Maps
  • Print Friendly Map
Upgrade Now

Cady Way Trail Description

The Cady Way Trail runs from the intersection of Aloma Avenue and Howell Branch Road/Hall Road (just east of Goldenrod Park in Goldenrod) west and south to Colonial Town Center (Fashion Square Mall) in Orlando. At the northern terminus, you can cross the road and pick up the Cross Seminole Trail.

The Cady Way Trail provides an excellent way for cyclists and pedestrians to link neighborhoods with shopping and business districts. The trail includes mirrors at blind corners and bridges over busy road crossings.

Parking and Trail Access

Parking is available at three main places:

Cady Way Park in Winter Park, FL. From SR 436 (Semoran Blvd), turn west on to SR 426 (Aloma Avenue) heading toward Winter Park. Proceed to Ranger Blvd. Turn south (left). Proceed to Cady Way and turn west (right) into the park.

Fashion Square Mall in Orlando, FL. From Interstate 4 in downtown Orlando, exit on SR 50 (Colonial Drive) and proceed east approximately 2.5 miles to Herndon Avenue; turn left. The trailhead is 0.5 mile north, adjacent to the Fashion Square Mall and the Post Office.

Winter Pines Golf Course: 950 South Ranger Boulevard, Winter Park; (407) 671-3172

Contact Information:
Orange County Parks and Recreation Department
4801 W. Colonial Drive
Orlando, FL 32808
(407) 836-6200

Cady Way Trail Reviews

My wife and I rode the trail round trip on January 20, 2018. We started at the fashion Square Mall. Construction (no doubt temporary) has destroyed the trail start and parking lot near the post office. We had to ride around the block and intercept the trail where it intersects Maguire. No big deal, but an annoyance nonetheless. The only worthwhile aspect of the next segment of the trail was the the fact that you could connect to a very nice trail that runs around Lake Baldwin and passes the community's downtown area as you circle the lake. The rest of the trail itself up to the big bridge overpass is quite forgettable. From the big overpass to the end of the trail is not even worth riding. Near the end of the trail there is an overlook at Perch Lake. The overlook was populated with a bunch of seedy looking people, although they seemed not to pay any attention to us on bikes. This trail gets one star for just there actually being a trail there and the other star for the access to the Lake Baldwin trail.

I had a good time, lots of friendly people. It was my first trail, didn't plan too much, but now I know that I need to know where the bathrooms are...

I had been riding on the Cross Seminole Trail for several months, and finally decided to ride it down to Cady Way Trail. The signs for the connection at Aloma and Howell Branch/Hall Roads are clearly marked, making it easy to go from one trail to the other. As with the other trails, you have street crossings which cut across the trails (or the other way around), and as with any street crossing you have to be cognizant of vehicles using the roadways before crossing. But, this should be first or second nature when riding a bike at a street crossing. Also as with most if the street or parking lot crossings, all have handicap crossing plates, or small curb water diversions which you get use to after riding on either of the trails a few times.

Going past Goldenrod Park, through the industrial cut through heading towards the 436 Overpass, this area is mainly flat with some minor hills/inclines. The next landmark is Cady Way Park, which is nice residential/school area. The trail then continues through the back part of Baldwin Park neighborhood and Lake Sussanah, and then to the trailhead at Fashion Square Mall. The trail scenery runs from urban, to industrial, to residential to park like, all of which are very beautiful and interesting. I had no problems navigating the trail, except where it ends/diverts near Lake Sussanah. Again, a quick glance at the TrailLinks map or website would have prevented this issue, but my first time out, I did a lap around the lake before returning to the trail at Beach Blvd. After riding to Lake Baldwin and Susannah a few times, I followed several riders continuing to Fashion Square, or in the opposite direction that I had previously rode. Following these cyclist, I was able to locate the trailhead at Fashion Square which was easy to find, if I had paid attention on my previous rides.

As with the Cross Seminole, Wekiva Trails. I haven't experienced any problems with traffic, traffic crossings, traffic noise, or lack of signage for crossings or trail directions (i just needed to pay attention). The rides on the trail are stress free, scenic and amazing. The trail is filled with walkers, runners, cyclists, or those just taking a break on one of the benches or picnic tables at the parks. The Cady is mainly flat, with light rolling hills, with one major overpass crossing at Route 436 (I usually take it in 5th or 4th rear cog). The trail is well maintained, and whether you have a road, mountain, commuter, or cruiser bike, either would work for use on the trails.


I would use it often if I lived here. There aren't as many street crossings as some of the other local trails. Combining it with the Cross Seminole Trail made for a great day's outing.

This trail runs behind housing developments, businesses, colleges and other community facilities. I think it would be very useful for getting around the area.

That said, it is not very scenic.

Also, finding the parking lot near the "Fashion Square Mall" end of the trail was difficult. There were signs for Anthem College parking lots, but not the trail.

Local residents might know where it is located, but better directions would be useful for visitors.

I have enjoyed my rides along the trail, mostly due to the parks along the way which provide the only true green space along this paved, well maintained path. It is too suburban and busy for my top ratings. Personally, I prefer a rural, scenic ride, although this is a good ride for those of us in the area. It is convenient and pleasant, so I will definitely ride again, just not a favorite.

I started my skate today on Cady Way Trail in Winter Park at Cady Way Park. I was really not expecting good skating conditions after the storm we had last night, but Cady Way Trail turned out to be quite a surprise. I was debating on using the connector and 436 overpass, but decided instead to head in the westerly direction towards the Fashion Square Mall.

When I started there were some water issues. I simply relaxed to recreational skate technique and minded my P's and Q's. Amazingly, debris from that storm was minimal. In fact, Cady Way Trail was better AFTER that storm than the Seminole Wekiva Trail is when there are no storms!!!!!

The first mile and a half through the trees was slower going thanks to the water and minor debris. Once I passed out of that area I was able to tuck down and begin to pick up speed.

I haven't been on this trail in a long time and boy has it changed and for the better! The old boardwalk is gone, replaced with a nice tour along the back side of Baldwin Park.

But the REAL surprise came when I got near Bennett Road. I was greeted by a sign indicating there were two directions I could go. What piqued my interest was a trail called Lake Susannah that I had never heard of before. I opted to take the north spur towards Lake Susannah.

The Lake Susannah Trail had some spotty areas from all the rain we have received this year and at its lowest point is starting to have some minor flooding issues. It wasn't insurmountable though so I continued on. I came across some construction issues, again minor from a group of condos being built. It was runoff sand from the rains we have been getting.

The real joy was when I hit the Lake Baldwin Trail. As soon as I set my speed skates on that trail the speed shot up. By the time I hit the West shore of Lake Baldwin I was clocking speeds in the 20 mph range.

Apparently though the normal users of that trail have never seen an inline speed skater before because I got more than my share of nasty looks. Never once was I unsafe, slowing down for any potential issues and passages, but they appeared to not like the speed I was approaching them at.

The Lake Baldwin Trail turned out to be a VERY fast trail! It took little to no effort to maintain a rock solid pace and it was relaxing to boot. A very scenic trail. Be aware though that on the Glenridge side the trail is cement and the tree cover there keeps the cement wet, causing mold on the surface. VERY SLICK! Inline skaters beware on pushes and cyclists on braking!

So my ratings for this sequence of trails; for inline skating it gets a rock solid A+, cycling it is going to take a hit or two since it is a busy trail and serious riders will not find it overly enjoyable other than the scenery so a B+ for that and runners get a HUGE A+ as well. For recreational use this trail sequence gets another HUGE A+!

I parked at Cady Way Park, changed at the pool bathroom and took off from there. There was some standing water when I left but by the time I returned a good portion of it had already evaporated. Overall this is a great trail. The Lake Baldwin portion gets busy and the users don't seem to like more serious users on the trail. If you are one of those, just be courteous and let them growl.

I ride the Cady Way trail frequently. It is a very nice, urban trail. It is well cared for, and convenient to reach via bike routes from downtown Orlando. There are good food options at the southern end at the Fashion Square Mall, as well as with a little detour into the Baldwin Park area.

When I lived in Orlando I used this path regularly to train for long distance races. I would park at the trail head behind the Fashion Square Mall and run from there, through Baldwin Park, and on over to Winter Park. The trail does not end there, it seamlessly connects into the Cross Seminole Trail and past that, on to the Seminole Wekiva Trail. In total you could run for up to 43 miles (or 86 roundtrip from trail to trail). I have run all these trails, at some point or another alone, as a young woman, and never felt threatened. There is a place in Baldwin Park that you can dip off and run around a lake for extra mileage, in Winter Park you run through a park where you can use porta-potties before hitting the suspension bridge over 436, and there are real bathrooms past that, when the trail turns in to the Cross Seminole. Lots of locals enjoying and training on this path too. I just used it again while visiting friends this past weekend and it was like a run down memory lane.

Rode this trail this afternoon and didn't even know I was on it.

I parked at the Cross Seminole Trail trailhead and realized that I forgot to lock my truck just after starting out on CST northbound. After heading back south to my truck and locking it, I noticed that the trail looked good in that direction so figured it'd just be a short run and scouted it out. Six miles later I came to the trailhead of the Cady Way Trail.

The trail is paved all the way except for, I believe two, wooden bridges. These were in pretty good shape and no problem for my tires. One of the cool aspects of the trail is the nice suspension pedestrian/bicycle bridge that crosses 436. Another nice feature is the mile markers starting at 0.00 to 5 3/4 miles. I don't remember seeing the 6th mile marker, but the end of trail sign is about 1/4 mile past the last sign (I also didn't notice the markers until the return trip to my truck after reaching the Cady Way trailhead).

Nice safety features on this trail are the asphalt quality and width, and mirrors placed strategically at two blind corners on the trail along with warning signs.

Your maps indicate that this trail intersects with the Little Econ Greenway trail (also mentioned by masaishigami in a previous posting). I believe I'll combine Little Econ and Cady for a nice 29 miler next time.

This was only my fourth ride on my new Trek (including Little Econ this morning), and I had a blast.


"The Cady Way Trail has now been extended from the Cady Way Trailhead in Winter Park (Orange County) to Goldenrod Park at the Seminole County line. The extension goes behind a neighborhood, with a mix of sun and shade, then over a new bridge (SR 436). Once over the bridge, the trail goes through some commercial spots, but still has grass on each side, benches, an occasional palm tree, scenic rest stop, more shade, then finally the Goldenrod Trail Head, at the Seminole County line. The Goldenrod Trail Head has a parking area, rest rooms, water fountains, shaded picnic benches, childrens' play area, and recreational facilities for tennis, volleyball, and basketball. "

"By chance, I bought a house 1/2 mile from the north trailhead of the Cady Way Trail. It is my favorite stretch, nice and shady, lots of vegetation, clean and well maintained. I enjoy it for walking, bicycling and walking the dog. The extension from the north trail head to Scarlet is open now. Not quite as pretty, but still nice. The stretch near the old navy base (new area of Baldwin Park) headed toward Orlando is distracting because of construction (equiptment noise, dust and dirt blowing, one construction crossover), but this too shall pass. I love Cady Way, at the Winter Park end."

"The trail is getting longer. A bridge over SR436 has begun so the trail will connect with two longer trails for a total of about 20 miles. Currently, if you take a right at the trail end then a left on SR436, you can pick up a dirt trail for about 1/4 mile then the rest of the trail is paved. It cross SR426 and becomes the Cross Seminole Trail. With a little finess, you can turn this into a three trail ride of over 30 miles (one way). "

"A new section is being constructed east of Cady Way Park. It was about 3/4 mile long on my visit last week, ending at Scarlet Rd. near Semoran Blvd. Speaking of construction, the section next to the old military base is particularly unattractive right now because of the construction of a huge development on the site.

All of the trail is not far from streets and buildings and therefore not very scenic. On the plus side, it is very wide, much of it divided into separate pedestrian and bike trails, and when I visited on a beautiful weekday, very little used. I'd encourage any visitors to Orlando who want a break from doing the usual tourist things to check this trail out."

"This is the original Orlando trail. Over the past couple of years, particularly with construction of Baldwin Park, the Navy Base replacement, the trail has become rough for inline skating."

"The Cady Way Trail is a nice short trail that mainly skirts residential areas in Winter Park. Getting to the trailhead at Fashon Square Mall is very easy and is recommended for those unfamiliar with the area. The end of trail in Winter Park is a bit harder to find unless you know how to get to the community pool. The north end of the trail is well shaded and very pleasant even on sunny Florida days. The southern end is exposed more to the sun as it rounds the Golf Course and then the military training center. None the less it is a pleasant ride or hike, and an excellent distance for a quick jog. The last time I visited there were no facilities for the Cady Way trail, just a Gazebo and a water fountain at the fashion Square mall end. A wise man will put up a cold drink concession!! I miss Orlando and the trails, I hope to be back soon when I retire and enjoy them again."

"One end is at the Orlando Fashion Square. The other end is Cady Way Park next to Showalter Field. Not terribly scenic, but the trail does skirt Winter Pines Golf Course and the new Baldwin Park development. It will ultimately be connected to the Econ Trail."

"Trail selection is inherent to our responsibilities and weather patterns. It’s good to optimize trail topography and weather to gain optimal time. Wind, rain, sun, route to and from work and home and the trail of responsibilities.

The heat season is upon us. Shade matters. The sun rises in the east and sets in the West. So these elements set our strategy for trail picks. East trails with morning sun and mature trees for dailey shade provide the best relief during our hot season. Cross Seminole is the coolest in the evenings but the trail's location is out in Oviedo (time, drive, tolls). Cady Way is also very shady, east sun oriented, and it is in a central location, Winter Park. The time to skate Cady is evening. Wait as long as you can till one hour before sunset. This will maximize coolness and reduce heat exposure. This is squirrel heaven. They will play chicken with you and race with you. But with shade comes chunkies! Watch out for chunkies. Chunkies are trail debris. "

Trail Events

This trail does not have any events yet.
Be the first to add one!

Add an Event

Nearby Trails

Orlando Urban Trail

Florida - 2.6 miles

Orlando Urban Trail offers a pleasant way for pedestrians and bicyclists to reach a number of recreational and cultural attractions in the city's...

Gaston Edwards Trail

Florida - 0.7 miles

In northern Orlando, the Gaston Edwards Trail provides a pleasant jaunt of nearly a mile along Lake Ivanhoe's eastern shore. (Hence, the trail is also...

Little Econ Greenway

Florida - 8 miles

The Little Econ Greenway trail is just one section of the Orlando area's many fine trails. features riverside recreation, picnicking, wildlife...


Gertrude's Walk

Florida - 0.25 miles

Gertrude’s Walk spans three city blocks in downtown Orlando, providing access to offices and the city’s sports arena not far from its southern end....

Cross Seminole Trail

Florida - 22.8 miles

Stretching from Orlando’s densely populated outskirts to the sleepy bedroom communities of Oviedo, Winter Springs, and Lake Mary, the Cross Seminole...

Kewannee Trail

Florida - 1.7 miles

Kewannee Trail is a charming, neighborhood trail in Maitland, Florida. More than just a recreation path, the trail is popular as a connective line...

Casselberry Greenway Trail

Florida - 5 miles

Casselberry Greenway Trail (formerly known as Wirz Trail) is a 5-mile multi-use path zig-zagging through Casselberry, Florida, linking neighborhoods...

Pine Hills Trail

Florida - 2.5 miles

Opened in 2017, Orange County's Pine Hills Trail spans 1.75 miles from Alhambra Drive to Silver Star Road in a western subdivision of Orlando. In the...

Seminole Wekiva Trail

Florida - 14 miles

Running along the former line of the Orange Belt Railway, the Seminole-Wekiva Trail offers a peaceful alternative to the busy streets of Altamonte...

West Orange Trail

Florida - 22 miles

Connecting small communities and suburban neighborhoods, the 22-mile West Orange Trail is one of Florida's most popular rail-trails, thanks to its...

Flagler Trail

Florida - 14 miles

A rail-trail that's a bit wild and off the beaten path, the Flagler Trail runs for around fourteen miles through rural Seminole County, to the...

Lake Apopka Loop Trail

Florida - 14.6 miles

The Lake Apopka Loop Trail is nearly 15-miles. There’s an abundance of nature as well as some background history regarding the lake. Spanning across...

Download the TrailLink mobile app and take TrailLink with you!
Get Your 2018 RTC TrailNation Jersey!
Donate and Get a FREE 2018 RTC Guidebook!

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Register for free!

Join TrailLink (a non-profit) to view more than 30,000 miles of trail maps and more!