Trail Running calendar near Osteen 2025-2026

Turkey Trails- Orlando, hosted by Bodies Race Company, is a Thanksgiving-themed running event in Orlando, Florida (ZIP 32789). The lineup includes 1 Mile, 5K, 10K, a Kids Dash, a Volunteer then Run option, and a Virtual Race. The event emphasizes family-friendly fun, with designer race shirts, custo..

Fit Together Fitness RC presents the inaugural Little Big Water River 5K Trail Run/Walk in Dade City, FL. The course starts on a narrow Florida Trail path (about 0.77 miles), then joins the wider blue trail around Withlacoochee River Park and returns to the starting pavilion. A 5K option and a 1-mil..

Jingle Bell Dash 5K Run/Walk is set on the campus of Bishop McLaughlin Catholic High School in Spring Hill, Florida. The cross-country style course spans the school’s 88 acres and winds through fields, trails, and open pavement, welcoming runners and walkers of all levels. The event supports the dev..

Bodies Race Company - Orlando presents the Candy Cane Course in Orlando, Florida, on December 14, 2025. The holiday-themed event offers multiple distances: 1 mile, 5K, 12K, plus a virtual race and a Kids Dash, with a Volunteer-Then-Run option. The 5K and 12K courses feature interactive maps and chip..

The Peace River 100 Miler is an ultramarathon held at Mosaic Peace River Park in Bartow, Florida. The course features a challenging 10-mile loop combining equestrian trails, sandy paths, rolling grass, and limestone roads. Runners face a 36-hour cutoff to complete the 100-mile distance, with aid sta..

Croom Zoom is a trail running event held in Brooksville, Florida, inside Withlacoochee State Forest. Runners tackle three distances on the Croom Park trails: 50K, 20M, and 10M. The course centers on a main 10-mile loop with a starter loop for the longer distances, weaving through oak hammocks and Fl..

Wekiwa Springs Ultra is held in Apopka, Florida (1800 Wekiwa Circle, 32712). The event offers three options: a 12-Hour Trail Run, a 24-Hour Trail Run, and a 24-Hour Relay Team, all based on completing as many 3.2-mile laps as possible. Runners experience a scenic, shaded loop through the Wekiwa Spri..

Long Haul 100 in Lakeland, Florida, is a premier 100-mile and 100-furlong trail race held at Colt Creek State Park. The course showcases Florida’s diverse, scenic landscape, with runners passing wildlife such as bald eagles, deer, alligators, otters, tortoises, and fox squirrels. The 100-mile option..

Monroe Cross Trail 50 Mile Ultra is a point-to-point ultramarathon in Florida, running 50 miles on paved trails from Rotary Park in Edgewater to Central 28 Beer Co. in DeBary. The course weaves along multiple rails-to-trails routes, with a Lake Monroe turnaround around mile 44, and also offers a 50K..

Forgotten Florida, a Run Bum Tours event in Christmas, Florida, offers a rare weekend trail challenge through Florida’s wild, seldom-visited landscapes. Distances include 100- and 50-mile point-to-point races that start together on Saturday, plus a 25-mile out-and-back for the 100; Sunday features 1..

The AdventHealth Nighthawk Trail Run takes place at Colt Creek State Park in Lakeland, Florida on Saturday, February 7, 2026. The event offers three options: Night Owl 5K (3.1 miles) Coyote 10K (6.2 miles) Nighthawk 15K Challenge - run both the 5K and 10K back-to-back All courses are loop courses..

Whispering Pines is a free, flexible trail running event held at Whispering Pines City Park in Inverness, Florida. Featuring a 5-mile loop of mixed single-track and double-track trails with packed sand and pine needle surfaces, the course offers gentle hills, ample shade, and two paved road crossing..

Skunk Ape’s Revenge is a multi-distance endurance event held in the Green Swamp – West Tract near Dade City, Florida (13347 Ranch Road, 33525). Participants choose among a 60k run, a 30k run, or a 30k Ruck. The course traverses swampy, wooded terrain for a rugged outdoor experience, with aid station..

AdventHealth Lake Apopka Scenic Trail 30K Run, 8 Miler & 5K is a Sommer Sports Events trail race at Magnolia Park, Apopka, Florida. Runners choose from three distances: a 30K loop (about 18.6 miles) along the Lake Apopka North Shore Trail, an 8-mile out-and-back to the historic Pump House, and a 5K..

Space Pirate 100 is an ultra-distance running event along Florida’s Space and Treasure Coasts, anchored at Cape Canaveral. Runners choose from four distances: a 100-mile solo, a 100-mile relay (3-person team), a 50-mile, and a 33.3-mile route. The course traces south along the Space Coast, past hist..

The Real Florida 5K and 10K is an annual cross-country race held at Wekiwa Springs State Park in Apopka, Florida. Celebrating its 39th edition in 2026, the event features an off-road course through scenic natural surroundings. Participants receive a commemorative T-shirt and medal, with awards for o..

Swamp 10k/30k/50k Trail Race, staged in Palm Coast, Florida by East Coast Trail Racing, offers 50K, 50K Relay, 30K, and 10K on rugged single-track trails. The course is described as beautifully challenging, featuring 2,345 feet of elevation gain on the 50K—the most for any Florida 50K. The event fos..

All Day at Holloway takes place at Holloway Park in Lakeland, Florida. The event offers four distance options: 10k, 30k, and 50k, plus a 50k relay in which five teammates complete the same 10k loop. It celebrates a day-long endurance vibe in a park setting, with a public, community-driven atmosphere..

Long Play Trail Run in Brooksville, Florida, takes runners on a single epic loop through the Croom Tract of the Withlacoochee State Forest. The event offers three distances: a 33.3-mile ultra, a half marathon, and a 6K, all beginning and ending at the Ridge Manor Trailhead along the Withlacoochee Ri..

Two Prairies Ultra is a FAT ASS ULTRA held near Fort McCoy, Florida, offering 50K and 30K options. The event, capped at 50 participants due to limited parking and a remote wilderness setting, starts at Pat's Island Trailhead in Ocala National Forest near Salt Springs. The course comprises two out-an..