Explore the best rated trails in Saint Leo, FL, whether you're looking for an easy walking trail or a bike trail like the Crosstown Trail and Seven Mile Loop Trail . With more than 49 trails covering 519 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.
This trail is great. Beautiful scenery, great downtown area, lots to do!
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.
This trail was our first of hopefully many rides in Florida. We used the trail head in Brooksville. Plenty of fee parking but reasonable at $5 (you’ll need the park mobile app). We went south for about 17 miles. Would agree with others that it is very noisy and also not very scenic. But it is paved which was nice. Bike traffic was very minimal. One set of restrooms 6 miles from where we started (at the athletic fields). Crossing traffic in some places was a bit daunting but in the very busy areas there were crosswalk traffic lights. We did see an armadillo on our ride back to the trail head we used. That was cool. All in all a great first Florida outing.
I rode the southernmost 15 miles which starts in Owensboro, near Dade City. There’s a dirt parking lot there, but no restroom. The trail is smooth asphalt about six feet wide. Beyond that there are trees on both sides. At some points you can see thru the trees and see some ranch like land until you get into the Withlachoochee State forest. About 5 miles into the ride there is a restroom stop. At about 11.4 miles the asphalt gets older and a bit rougher but still is good- no tree roots or potholes. There is limited shade. At mile 15 we got off the trail and had lunch at Brees Riverside cafe. shade
The paved trail is wide and accommodates its users. My running app indicated the distance is a bit less than 4.5 miles (closer to 4.1) but it was a nice way to spend the morning.
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.
We rode this for the first time today. It was cooler outside so not too many people. It was beautiful!! Highly recommend if you’d like an easy ride.
I grew up driving over this bridge with my parents. It was great fun to ride my bicycle over it as an adult. We parked at Cooper’s Bayou just east of the bridge entryway—a good place to park and ride the entire trail. Whiskey Joe’s was a fun place to eat/drink. Be prepared for crowds there on good weather days. I will ride this trail again next year.
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.
We rode the trail around Dunedin area to Clearwater and on over to Clearwater Beach. We also rode from Dunedin North to Palm Harbor area. The Dunedin area has lots of places to eat/drink right off the trail. Mileage markers are not easily visible. The 20 MPH limit is ignored by cyclists and other people on various wheeled creations. “On your left” isn’t followed either.
My friend and I rode this trail during our February visit to the area. It does get a little confusing down below the city library, but we were able to navigate over to the circular path leading across the water to Clearwater Beach. A beautiful view and a fun ride.
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