Explore the best rated trails in Winter Park, FL, whether you're looking for an easy walking trail or a bike trail like the Ponce Inlet Trail and Cross Volusia Trail . With more than 50 trails covering 380 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
Did the entire trail (both fragments) at 52 miles on rollerskates. Great surface and one of the best long trails in Florida for skates. Beautiful scenery. Saw bald eagles, an owl, a couple of deer, and lots of gopher tortoises. I will say that the northern fragment has like no place to park. I parked at the National Refuge but that isn’t an official trailhead. Additionally, the northern leg has some areas that are just sidewalk vs actual path. Still enjoyable !
The northern portion is gorgeous with Waterview to the west and a nice ride through beautiful parks. I went a little further and did the regional trail just north of this one and it was absolutely beautiful but very short. The section after the high school heading north is dangerous for unsteady cyclist. The local community is actively working to improve this 3 to 5 mile section of trail Once that is complete the trail will be quite nice. The majority of the trail is a double wide sidewalk, so it is not good for a zone four or five ride. It is perfect for a leisure zone 2 ride. The Northern section is excellent for a family bike ride. On my way back heading south. I avoided the double wide sidewalk and rode the generous bike lane until it ended.
This is a short city trail ride but well maintained. There are sections of it which are quite pretty. There are amenities along the way, and with a Dunkin Donuts, 7-11, and a Diner at the trail end.
Very disappointing. Nothing special about the trail itself. the homeless encampment and trash was unsettling. Also many men loitering about. I did not feel safe. So many other nicer places to bike this is just not worth it.
This was nice and level, easy parking at either end, part sun and part shaded (although mostly sun), but you will be passing by a few homeless encampments. No one came out to bother us, but just something to be aware of your surroundings. As an older female rider, I probably wouldn't do this ride again alone. But it was an interesting ride, nonetheless. When we got to the end in downtown Leesburg, there are lots of great places to eat.
I started this trail at the southern entrance. I got less than 3 miles into my bike ride and turned around. Too many intersections with heavy traffic. Perhaps this trail is better towards the northern end.
I ride this area at least twice a week. The trails are wide & the scenery is pretty good. It is great place to ride at night if you enjoy that. The neighborhood is always well decorated at Christmas.
On our visit to Florida and first time in the saddle in six months we opted for a short day, about 20 miles. We parked at the Copper library which was convenient and had nice bathrooms and water. There are new developments and a shopping complex since the details to this trail were written. At about mile 5 there is a Publix, Starbucks and a few more retail stores. There were a lot of roads to cross and hills to climb. We opted for a 6 mile round trip down the intersecting Lake Shore trail to Minneola Lake. That was a nice, scenic section. Overall a good day to start our season.
Cute little trail. Very smooth with many boardwalks. Perfect short ride after a day at Kennedy Space Center. Blessed with a red shoulder hawk!!!!
Rode on a cold day but still saw otters and deer. Be careful because Google maps will take you the wrong way. The northern most part of the trail is in Mabel FL off Highway 50. The access road to this point is horrible but short.
Has cute scenery! Lots of it is boardwalk, but smooth even as a boardwalk! As a distance skater, it was still easy and enjoyable. Averaged 9 mph on skates. Easy surface and saw a red shoulder hawk which is always a treat :)
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