Trail Running calendar near Sarasota 2025-2026

The Day Before Mother's Day 5K is a vibrant running event taking place on Fort Myers Beach, Florida, on May 10, 2025. Participants can choose from a live 5K run/walk, a virtual 5K, or an untimed 1-mile fun run/walk. The event aims to promote community engagement and wellness, with a portion of the p..

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 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 Durty B-EE-RR-UN 6hr is a self-supported, low-key running event held in downtown St. Petersburg, Florida, at Flora Wylie Park. Participants run a roughly 3.6-mile loop along waterfront sidewalks, including the St.Pete Pier and nearby parks. The race lasts six hours, challenging runners to comple..

The Pinellas Trail Challenge is an ultramarathon event that takes place along the scenic Pinellas Trail in Florida. This out-and-back race begins in St. Petersburg, extends to Tarpon Springs, and returns to Dunedin, covering a distance of just over 46 miles.Participants can enjoy the beautiful surro..

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..

The Tick Tock Ultra is an exciting endurance event taking place at Lake Hollingsworth in Lakeland, FL, featuring both 12-hour and 6-hour challenges. Participants will race along a scenic paved walkway, aiming to complete as many 2.84-mile laps as possible within their designated time. The event incl..

The Tampa Bay 100 Mile Endurance Run is a unique urban ultramarathon held in Tampa, Florida, starting in historic Ybor City and finishing in St. Petersburg. This point-to-point 100-mile course showcases Tampa Bay's vibrant culture and scenic beauty, passing through Safety Harbor, Dunedin, Clearwater..

The Colt 45 Trail Run is an exciting running event taking place at Colt Creek State Park in Lakeland, Florida. Participants can choose from four distances: a challenging 60-mile "Colt Double Malt," a 45-mile "Original Colt 45," a 45K "Colt Silver," and a 14-mile "Colt Mini." The course features scen..

The Legacy Trail Ultra is a free 60K ultramarathon held annually in Sarasota, Florida, sponsored by the Manasota Track Club. The race follows 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 ti..

Caloosa Fest Ultra is an exciting annual running event held at Caloosahatchee Regional Park in Alva, Florida. The event features a 50K ultra marathon and a 25K race, both set on a scenic 11.1-mile loop that includes diverse terrain, beautiful views, and technical stretches. Participants can enjoy ai..

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..

RunFluent Christmas 2025 is a festive running event held in Lutz, Florida, featuring a 4-mile race and a unique 7-hour multi-lap challenge. Participants can compete for awards, including top finishers and special recognitions such as reaching a 50k distance within the time limit. All finishers recei..

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 running event taking place in Colt Creek State Park, Lakeland, FL, featuring a challenging 100-mile race and a 100-furlong (12.5 miles) option. This Western States Qualifying Race is designed for both novice and experienced runners, offering a scenic course that showca..

The Coo-Wah-Chobee 50k, 25k, and 5k is an annual trail running event held at Carlton Preserve in Venice, Florida. Organized by RunFluent, the race features a single-loop course with a mix of single and dual-track trails, offering challenging and scenic routes for participants. The event includes opt..

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 known for its fast, well-groomed terrain that blurs the line between trail and ro..

The Funest 50K @ Carter Rd is an exciting running event taking place in Mulberry, Florida, featuring challenging courses of 50K, 30K, and 10K. Set in the scenic Loyce E. Harpe Park, participants will navigate rolling hills and dirt trails, making it a tough yet enjoyable experience.The event is limi..