Trail Running Calendar Florida 2025-2026

The Lake to Ocean 100K is a sold-out, point-to-point ultramarathon held in Florida, starting at the NENA trailhead in Port Mayaka and finishing at Hobe Sound beach. Recognized by Outside online as one of the top 10 most beautiful trails worldwide, the course features mostly single-track remote trail..

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..

Moon Over Croom is an evening trail running event held at Croom Park in Brooksville, Florida. The race features three distance options: 21 miles, 14 miles, and 7 miles, all run on a well-marked 7-mile loop combining the B-C Loop and C-Loop trails. Participants run in the dark, using headlamps and gl..

The Florida Run LEFTOVER Trail Race is an exciting annual event taking place in Clermont, Florida, featuring both 4-mile and 8-mile trail runs. Scheduled for June 14, 2025, this race aims to utilize leftover medals, shirts, and other items, promoting sustainability while providing participants with..

The Miami 50/50 is a unique 50-mile urban ultramarathon held in Miami, Florida, featuring a two-person team format where both runners complete the entire distance together. The race course winds through iconic Miami neighborhoods such as Wynwood, Miami Beach, Key Biscayne, Calle Ocho, Coconut Grove,..

Toxic Trail 37 is a challenging 37-mile road race held in Canal Point, Florida, running from Port Mayaca to Stuart Beach. The course highlights environmental awareness, focusing on the toxic water discharge from Lake Okeechobee into the St. Lucie River and the Atlantic Ocean.The race features a mix..

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 Vero Beach Octopus Ultra, held in Vero Beach, Florida, is a unique multi-distance ultramarathon featuring a central base with eight out-and-back "Octo-Arms." Runners can choose distances from a 5K dash to a full 100-mile race by completing various combinations of these arms. The course offers a..

The Sombrero Sizzler is an annual timed running event held in Jacksonville, Florida, featuring distances of 3, 6, 9, or 12 hours on a flat, fast 1.25-mile loop course. The course, located on the former Cecil Field military base, is mostly paved with asphalt and concrete, shaded by pine trees, and in..

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 Trident Trail Races, held in Jupiter, Florida, is a challenging series of trail running events set on the ancient sugar sand dunes of the Jupiter Ridge Natural Area. This unique venue features soft sand terrain with up to 1,200 feet of elevation gain, making it one of Florida's toughest trail ra..

The River to Sea 12/6 Hour Trail Race takes place in Palm Coast, Florida, featuring a nearly one-mile loop trail surrounded by palm and oak trees in a classic old Florida hammock setting. The course is flat, shaded, and nontechnical, offering a scenic and comfortable running experience between the r..

Sufferfest on Section 4 is a challenging 5-hour endurance event held in Middleburg, Florida, along the technical and hilly Section 4 of the Pioneer Trail. Participants traverse a roughly 2.5-mile out-and-back single-track course featuring switchbacks and scenic overlooks of Black Creek. The event em..

The Hot August Night Trail Race is an exciting night running event taking place in the Citrus Tract of the Withlacoochee Forest, Inverness, FL. Participants can choose from three distances: 5 miles, 10 miles, or 20 miles, all set against the backdrop of a beautiful forest under the stars. The course..

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 Wildcat Ultras is an ultramarathon event held at the Escambia County Equestrian Center in Pensacola, Florida. The race features multiple distances including 100 miles, 100K, 50 miles, 50K, and 15 miles, all run on a 2.5-mile loop of mostly grass and dirt with minimal elevation change. Known for..

S.O.S. in Middleburg, Florida, is a unique running event held on the scenic Sandridge Trail within Jennings State Forest. Participants can choose from a 9K distance or time-based challenges of 3, 6, or 12 hours, all run on a 2.75-mile loop.The race features a cupless format, encouraging runners to b..

The Wild Boar Night Run is a half-marathon trail race held at the Green Swamp Wilderness Preserve - West Tract in Dade City, Florida. This out-and-back course features old forest roads, pasture lanes, and the Florida Trail, offering runners a unique nighttime experience surrounded by natural sounds..

The Riverbend Ultras 12 HR/50K is a community-focused ultrarunning event held at the River Pavilion on Picnic Island in Riverbend Park, Jupiter, Florida. Participants can choose between a 12-hour run, a 50K, or a fun run. The course features scenic 3.2-mile loops along the Loxahatchee River on grave..

The Osprey Trail Run is a scenic trail running event held at the 94-acre George LeStrange Preserve in Fort Pierce, Florida. It features two main race distances: an 8K (about 5 miles) consisting of two loops, and a challenging 25K (about 15 miles) made up of six loops around a course that includes te..