Trail Running calendar near Oakland 2026-2027

A 30 km night trail run through the diverse and wildlife-rich terrain of Florida's Green Swamp. The event features a supportive atmosphere with no time cut-off and a festive post-race potluck. It's part of a larger trail series and is marke..

A night trail event at Holder Mine Campground in the Withlacoochee Forest offering 5, 10 and 20 mile single-track courses. Headlamps are required and courses are marked with reflective pins and glow sticks.

The Wild Boar Night Run is a half-marathon trail race through Florida's Green Swamp West Tract. Held at night in September, it features a stocked aid station and a festive post-race potluck party. All finishers receive a choice of a commemo..

Enjoy a run or walk along the paved Pinellas Trail in Dunedin with a festive finish at HOB Brewing Company. Participants receive a medal, t-shirt, and a craft beer for those over 21.

The Itch is a rugged, point-to-point 50K trail race on the Florida National Scenic Trail. Runners navigate using orange blazes and must carry a phone with the course GPX. This no-frills event offers aid stations and a drop bag point in the..

Hit the Pinellas Trail for a Halloween-themed run supporting veterans. The Camo & Cobwebs event offers a timed 5K and an untimed 1 Mile Fun Run/Walk, both starting and finishing at de Bine Brewing Company. Expect costumes, finisher medals,..

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.

This Halloween trail race offers a spooky evening on the Florida Greenway. Choose from 5k, 10k, or a combined challenge in either run or ruck divisions. Costumes are encouraged, and all finishers get a medal.

Run the shaded, single-track trails of the Mala Compra Greenway, just steps from the Atlantic Ocean in Palm Coast. Choose from 50K, 24K, or 12K distances on this looped course. All finishers get an award, and free kids' races are also part..

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.

Experience the natural beauty of Florida at Lake Louisa State Park with a 5k, 10k, or Half Marathon trail run through lush pine forests and scenic lakeshores. Enjoy a chip timed race complete with finisher medals and post race food.

Join this patriotic honor run on the scenic Pinellas Trail to celebrate military veterans. Choose from 10K, 5K, or Kids Dash distances in a stroller friendly environment at Dunedin.

Honor America's veterans at this scenic out and back race along the paved Courtney Campbell Causeway Trail. Choose from multiple timed distances and enjoy panoramic views of Tampa Bay while supporting veteran suicide prevention.

Explore Tampa Bay on foot in this unique 100-mile urban tour. The point-to-point route winds from Ybor City to St. Petersburg, passing murals, beaches, and city landmarks. It's a self-reliant adventure with a 36.5-hour cutoff to earn your f..

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.

Experience a team relay through the shaded pine forests and palm trees of Alafia River State Park. Run together in teams of four or eight and enjoy a festive weekend village with campfires and star lit camping.

Holiday races in downtown Dunedin at HOB Brewing Company offer 5K, 10K (2 loops) and 15K (3 loops) on a paved, timed course along the Pinellas Trail, with medals, event shirts and a post-race beer for participants over 21.

The Long Haul 100 is a Western States qualifying trail race in Florida's Colt Creek State Park. Runners can tackle a 100-mile loop course or a shorter 12.5-mile option on the scenic trails.

Explore Florida's wild trails on a unique point-to-point ultra or shorter loop races. The courses wind through scenic state forests and palm groves, offering a chance to see diverse wildlife. Part of the proceeds supports local trail mainte..

Blast off on a coastal adventure where space meets piracy. This crew-supported ultra takes runners along Florida's scenic Space and Treasure coasts. The journey ends on the beach with a unique treasure chest finish.