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.

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.

A trail event in Palm Coast Florida featuring 50K, 24K and 12K loops on mostly single track near the Atlantic Ocean. The field is limited to 125 runners and all finishers receive shirts and awards.

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.

November 2026

Trail run at Lake Louisa State Park on November 7 2026 offering 5K 10K and half marathon across varied trails with aid stations and age group and team awards.

Celebrate Thanksgiving with a series of themed races including a Half Marathon, 10k, and 5k in Orlando. Enjoy chip timed results, finisher medals, and family friendly distances like the Kids Dash and 1 Mile fun run.

Dunns Ultra Marathon Badasses runs an 11.75 mile loop at Dunns Creek State Park near Pomona Park, Florida, offering multiple ultra and ruck distances, two on course aid stations and a runners village with hot food and overnight support.

A timed endurance event at Ravine Gardens State Park in Palatka, Florida offering 12 hour, 24 hour, 50K and 50 mile formats on a paved USATF measured two mile loop. Aid stations and mandatory personal lighting are provided.

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.

Experience the natural beauty of Lakeland at Colt Creek State Park for a trail event featuring distances from 14 miles to a 60 mile ultra. Enjoy a loop based course with handcrafted medals and a post race picnic.

Trail ultraruns at Lake Louisa State Park in Clermont, FL offering 50K and 25K on a 16.2 mile loop with mostly singletrack, varied terrain and about 700 feet of elevation on the 50K. Four aid stations and professional timing are provided.

December 2026

Celebrate the holidays at the Candy Cane Course in Orlando featuring distances from a Kids Dash to a 15k. Enjoy chip-timed results, designer shirts, finisher medals, and festive treats at the finish line.

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.

January 2027

A trail event at Colt Creek State Park offering a six-loop **100-mile** race and a single-loop **12.5-mile** 100 furlongs course with staffed aid stations, looped drop bag access, and a rollover credit policy.

A multi-distance trail event in Christmas, Florida on January 30 and 31, 2027, running through Tosohatchee and nearby state forests with single track, varied terrain, wildlife viewing, course maps, aid station details, and crew and voluntee..

February 2027

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.

An ultramarathon on Florida’s Space and Treasure Coasts offering 100 mile, relay, 50 mile and 33.3 mile options. Field size is limited and all events require a support crew.

March 2027

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.

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