Explore the best rated trails in Highland Park, FL, whether you're looking for an easy walking trail or a bike trail like the Chain of Lakes Trail and Auburndale TECO Trail . With more than 26 trails covering 194 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.
It didn’t have a ton of scenic, but there was a lot of shade so even if it was in the middle of the day, there was places where you could drive without being in full sun… I have ridden in about a year or so 14 mile ride was still doable my ride just
Nice trail but not marked very well. If I was not following the map on trail link I wouldn't have any idea where I was. Part is just old sidewalks. You can start and stop at the Osceola welcome center on 192 but still no sighs for the loop trail
My husband and I rode this trail today (3-31-26) and had a great experience. The trail is well-maintained and the downtown area is so cute. We stopped a couple of times for lunch and coffee. I would highly recommend this trail. Beautiful trees and open spaces, with lots of rest stops throughout the ride.
There don't seem to be many outdoor spaces left in crowded central Florida that offer a quiet, removed experience. This trail has it in abundance, however. Running straight as an arrow through grazing lands, forest, and wetlands, it's almost a Zen-like experience as you cruise silently along the miles. Most activity is near to the trail starting points, so after a few miles away from those, you're left to yourself. One of the best, for sure.
My brother in law and I rode this trail 2/23/26. We were in the area so hopped on the trail doing the loop from Bruce B Downs. Cold day but really enjoyed it. On our way back to Venice we stopped in Ybor and had lunch at the Columbia. Fun day.
Rode the path ,rode a gravel trail and grass trail . bogged out in the sand. Nature. Nice clean restrooms , water stations . Perfect day.
The trail was about 10’ wide And definitely no bathrooms. Very desolate very very few people around we went on a Saturday afternoon. Cloudy it probably would’ve been hot if the sun was out it was 75 and cloudy if you like cows and trees you would enjoy it. We went about 7 miles and turned around. We sort of liked this path but other than that it was boring I thought and so did my wife. We started on the south end by Auburndale Trail and continued on to this trail about
¿. You can ride along The path and see the huge sports complex. Beautiful dog park fenced in and playgrounds - all types of stuff for people to do - benches for sitting on the sides of the trail. The trail is blacktop about 10 foot wide very smooth besides some spots. We started at the south end and went north to General James A. Vann Fleet State Trail and continued on that trail for another 15 miles then turned around and came back
I didn't care for this trail. Its all on uneven sidewalks in front of houses and you never know when someone pulls out and stops in the bike lane.Then you have to ride on route 98 which is also on sidewalks with busy *** traffic.
After years of traveling to Central Florida to visit theme parks, this December I convinced my family to spend a day on bikes as a break. We rented four bikes from Bikes and Blades at the Killarney Station and rode almost halfway (10 miles) down the trail towards Apopka. The width of the trail was superb for family bike riding, with a smooth asphalt surface throughout. Signage was clear and easy to follow. Downtown Winter Garden is a true gem. We stopped on the way back, parked our bikes and explored the many restaurant and shops. I plan to come back and ride the full length of the trail, including the connections to Lake County to the west.
Me and my family drove an hour to get there for the bike trail. We parked by the dock parking which was beautiful to see. Lots of scenic views. When we start to ride the trail it took us out on the main road, about 2mins in the ride we end up on a road closer that we could not go around. That was the end of our ride.
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