Trail Running calendar near Osprey 2026-2027

Join the festive St. Patrick's Day run in Dunedin on the flat, paved Pinellas Trail. Choose from a 5K or 10K course, both starting at HOB Brewing Company. The event includes a medal, tech shirt, and a post-race party in a family and pet-fri..

Run the trails at Colt Creek State Park on April 11, 2026. Choose from a 5K, 10K, or Half-Marathon distance. The event features chip timing, aid stations, and post-race awards.

The Turtle Trot 10K & 5K is a run/walk at SunWest Park in Hudson, Florida, on a paved path circling old salt mines. Every participant gets a finisher award, and proceeds support the PAIR program for inclusive recreation. T-shirts are availa..

Kick off the Dunedin Highland Games with this 5K trail run and walk. The scenic course starts and finishes at Highlander Park, venturing into Hammock Park. Registration includes a t-shirt, medal, and entry to the festival with Celtic music..

Join the Kraken in Sarasota for a 5k or 10k race featuring finisher bottle openers and t-shirts for all runners. Enjoy a community event with awards for top performers across multiple age groups.

Tackle the rolling hills and sandy trails of an old phosphate mine at the Funest 50K. This event offers 50K, 30K, and 10K distances on a challenging 10K loop course in Loyce E. Harpe Park. Runners can enjoy post-race food and support trail..

Experience a unique trail and beach run through mangrove estuaries and coastal dunes at Lovers Key State Park. Choose between a 5k run or 1 mile fun run with proceeds supporting local park preservation.

Experience a unique sunrise run on the beautiful sands of Englewood Beach featuring a 5K and 1 Mile fun run. All finishers receive a custom sea turtle beach towel and a special magnetic medal.

Experience the 3rd annual Race for the Planet 5K at Babcock Ranch. Enjoy a scenic route through trails and sidewalks in Punta Gorda with timed and untimed options for all participants.

Run through the scenic woods of a 250-acre camp in Punta Gorda. This trail run offers 5k, 10k, and 15k distances with proceeds supporting a local school. Enjoy a family friendly day with a kids dash and post race food.

A 5K at Robinson Preserve in Bradenton on June 13, 2026, offering participant t-shirts, snacks and post-race hotdogs, age-group awards for male and female finishers, and a guided pre-race stretch session.

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.

Celebrate Halloween with the Trick or Trot 5K at Ann and Chuck Dever Regional Park on October 17, 2026, featuring a 5K trail run and 1 mile walk on scenic dirt and gravel paths. Wear your best costume for prizes, grab a shirt and medal, and..

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,..

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.

A trail running event at Carlton Preserve in Venice, FL on November 28, 2026 offering a half marathon, 10k and 5k with race shirts, post-race snacks, age-group awards, vendor booths and music.

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.