Explore the best rated trails in Oldsmar, FL, whether you're looking for an easy walking trail or a bike trail like the Withlacoochee State Trail and Coastal Anclote Trail . With more than 32 trails covering 393 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.
Really pretty trail with great views and not too many inclines. Good workout but also super scenic and a great length. Highly recommend!
Very well maintained. Smooth ride. Approximately 6.5m from Lot 8 to East trailhead. Connects into the Suncoast Trail on the east end. About 80% sun so wear sunscreen and bring water. Saw dear. barred owl, woodpecker. Highly recommend
The route I went on was siren, and well kept up. It's now ine of my favs. I wish it was closer to me. ¿
We parked at Lake Townsen Park, had some lunch at Bree’s Provisions (They close at 2:00) and rode north, out and back for about an hour. The trail is well maintained and goes through beautiful farm country.
What a beautiful day on this part of the trail... well maintained, some many places to stop, site seeing, Sponge Docks, Monkey Farm, Shopping, Restaurants and libations.
The trail and the land needs to be cleaned up. The grass and weeds needs to mowed and garbage in the grass. The weeds are as high all along the trail by Trinity Blvd. You have a nice trail but the surrounding areas are filthy. It makes the homes /townhomes look shabby. How come Starkey doesn't have weekly maintaince on this empty lot???. She made promises when she was running telling us that this is going to be beautiful. Why not put some lights up for the darkness when walking or riding on this trail?????? The area around this trail is filthy and needs attention Asap!!!!!!
Parked at the Shamrock Nature Center. The waterway park trail south of the water meets the south end of the legacy trail. Ride north to Osprey Point trailhead, about half of the Legacy Trail. Trail is an excellent ride, very popular
It is a dream ride, all paved, scenic views from beginning to end. Stop off at Whiskey Joe’s for dinner or cocktails. Sandy beaches to sit on - easily make a day of this one trail and not wear yourself out.
We started at the Pinellas Trail North, the beginning point, and rode 10 miles out to John Chestnut Park. The first 2.5 miles runs alongside a preserve so quiet, scenic & very family friendly. The rest of the ride was along the highway so continual road noise although every major intersection had a button for the crosswalks, the trail is well paved & wide. There was no signage for parking at the trail head or restroom facilities. Signage to guide you to Tarpon Springs is also very limited.
We rode our tandem on the Courtney Campbell Causeway on a bright, beautiful Super Bowl Sunday, 2/9/25. The asphalt still has a few sections where the pavement has been lifted and so is rough, but it is very serviceable with most bumps avoidable. The pelicans were diving and feasting on bait balls across the bay as we rode. The trail was busy, especially near the parks in the causeway, but nothing that a bit of patience didn’t resolve. It is a wide multiuse trail. We used a parking area in Cooper’s Grove Park in Del Oro Grove on the west side of the bay. We rode out and back and explored Safety Harbor (nice!) and some additional areas after our out and back.
Training for a sprint Triathlon and used this for interval training. Not much shade but the perfect length for beginners and early training.
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