Trail Running calendar near Osteen 2026-2027
We have found 41 Trailruns within 80 miles of Osteen. See below where and when you can find the races.
We have found 41 Trailruns within 80 miles of Osteen. See below where and when you can find the races.
Orlando Spartan Weekend at Lake Nona on Oct 10 and 11, 2026 features obstacle course events from a 5 km sprint with 20 obstacles to a 10 km super with 25 obstacles. Team entries can secure shared start times and verified discounts are avail..
A point-to-point 50K on the Florida National Scenic Trail Western Connector near Ocala, Florida, with minimal course markings so runners must carry a phone and download the GPX; aid stations and one drop bag location are provided.
Experience an off-road 5k trail run with your dog at Rock Springs Run State Reserve. This dog-friendly event features a spooky theme, finishers medals for both humans and pets, and supports local animal rescues.
Celebrate Halloween with a spooky 5K in Clermont. The evening event features haunted zones, a costume contest, and a live DJ. A virtual 5K option is also available.
A fully supported, point to point 200 mile trail run across Florida featuring long sections of the Florida Trail, mixed terrain, stocked aid stations and GPS tracking, with a 96 hour cutoff and cash prizes for top finishers.
Savage Race and Savage Blitz come to Dade City, Florida on November 14, 2026, with new obstacles and multiple course options. Tiered ticket pricing applies, no extra checkout fees are added, and on-site parking is $20.
Sleigh It is a looped event at Lake Wailes Park offering a 5 Mile option plus 6 hour and 12 hour timed formats. The 5 mile loop runs on grass and asphalt with aid stations at each turnaround.
A free, donation-supported 12 hour trail event at Whispering Pines City Park with a 5 mile loop, an aid station and a finisher award for 10 miles. Capacity is 185 and there is no waitlist.
Experience a unique single loop trail run through the Withlacoochee State Forest featuring 33 1/3 mile, half marathon, and 6K distances. Enjoy riverside trails and celebrate your finish with a post race barbecue and handcrafted medals.