Trail Running calendar near Sarasota 2025-2026

The Flatwoods Fun Run, also known as The Wally World Loop, is a 33-mile fat ass ultra run held in Thonotosassa, Florida, through the Lower Hillsborough Wilderness Preserve. This low-key, adventure-style race emphasizes exploration over competition, featuring a challenging course that includes single..

The Saunders Lakeland Mountain Marathon (SLMM) is a challenging two-day mountain navigation race held annually in the Central Lake District, UK. Teams of two runners navigate rugged terrain over six linear courses of varying distances (27 to 54 km) and difficulty, plus a 12-hour score course where t..

The Skunk Ape Night Run is a 30K trail running event held at the Green Swamp Wilderness Preserve - West Tract in Dade City, Florida. This unique night race showcases a variety of Florida terrains, including pasture lanes, mud, dirt roads, single-track trails, sugar sand, and fire berms. Runners expe..

The Pinellas Trail Challenge is a 46-mile ultramarathon held in St. Petersburg, Florida. This out-and-back race follows the scenic Pinellas Trail, starting in St.Petersburg, heading north to Tarpon Springs, and returning to Dunedin. The event offers runners a unique opportunity to experience the nat..

The Wild Boar Night Run is a half-marathon trail race held at the Green Swamp Wilderness Preserve - West Tract in Dade City, Florida. Organized by Skunk Ape Events, this night run features an out-and-back course along old forest roads, pasture lanes, and the Florida Trail, offering runners a unique..

Tick Tock Ultra is a challenging timed running event held in Lakeland, Florida, at Lake Hollingsworth. Participants can choose between 12-hour and 6-hour solo races or a 12-hour relay for teams of 3 to 5 runners. The course consists of repeated 2.84-mile laps on a paved walkway around the scenic lak..

The Tampa Bay 100 Mile Endurance Run is a unique urban ultramarathon held in Tampa Bay, Florida, organized by Skunk Ape Events. Starting in Ybor City, the point-to-point course covers 100 miles through Tampa, Safety Harbor, Dunedin, Clearwater, Gulf Blvd, and finishes in St. Petersburg at Vinoy Park..

The Colt 45 Trail Run takes place at Colt Creek State Park in Lakeland, Florida, offering a variety of challenging trail distances. Runners can choose from a 60-mile "Colt Double Malt" (four 14-mile loops), a 45-mile "Original Colt 45" (three 14-mile loops plus a 3-mile starter loop), a 45K "Colt Si..

The Legacy Trail Ultra is a free 60K ultramarathon held annually in Sarasota, Florida, organized by the Manasota Track Club. The race features an out-and-back course along the scenic Legacy Trail, starting at Payne Park and heading south for 18.6 miles before returning. Participants have a 10-hour t..

The Caloosa Fest 5K is an exciting running event taking place in Alva, Florida, featuring a scenic trail run. Scheduled for December 6, 2025, this festival includes not only the 5K race but also ultra races of 25K and 50K, along with adventure races. Participants can enjoy various activities, includ..

The Caloosa Fest Ultra, held at Caloosahatchee Regional Park in Alva, Florida, features challenging 50K and 25K trail races on December 6, 2025. The course consists of an 11.1-mile loop with varied terrain, including rolling hills, technical stretches, and scenic views along Green, Black, and Blue t..

RunFluent Christmas is an annual running event held in Lutz, Florida, featuring a festive atmosphere and multiple race options. Participants can choose between a 4-mile run or a 7-hour multi-lap race, including a 2-person relay. The event offers race day T-shirts for all participants and finisher aw..

The Peace River 100 Miler is an ultramarathon held at Mosaic Peace River Park in Bartow, Florida. The course features a scenic loop of at least 10 miles, combining equestrian trails, sandy paths, rolling grass, and limestone roads, with aid stations every 2-3 miles. The race offers a challenging yet..

The Long Haul 100 is a premier ultramarathon held at Colt Creek State Park in Lakeland, Florida, featuring a 100-mile race and a shorter 100-furlongs (12.5 miles) event. The course consists of six 16.7-mile loops through scenic Florida wilderness, home to diverse wildlife such as bald eagles and all..

The Coo-Wah-Chobee event, held in Venice, Florida, offers 50k, 25k, 5k, and youth 5k races on a single-loop course through Carlton Preserve. This scenic park features a mix of single-track and dual-track trails, providing a varied and engaging running experience. Organized by RunFluent, the event is..

All Day at Holloway is a running event held at Holloway Park in Lakeland, Florida, offering multiple distance options including 10k, 30k, 50k, and a 50k relay with five runners each completing a 10k loop. The course is a well-groomed, fast cross-country trail that blurs the line between trail and ro..

The Funest 50k @ Carter Rd is a challenging trail running event held at Loyce E. Harpe Park in Mulberry, Florida. Offering 10k, 30k, and 50k distances, the race features a tough course with rolling hills and twisting sand and dirt trails through an old abandoned phosphate mine, now popular mountain..

The Gator Wilderness Camp Trail Run/Walk is a scenic event held at Gator Wilderness Camp School in Punta Gorda, Florida, featuring 5k, 10k, and 15k trail races through diverse woods and shaded hammocks on 250 acres. The event supports a residential school for struggling adolescent males and offers r..