Trail Running calendar near Englewood 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.

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.

Run the Dunedin Oktoberfest 5K or 10K along the scenic Pinellas Trail, finishing at HOB Brewing for postrace Oktoberfest vibes. Stroller and dog friendly with a beer armband for 21 and over and finisher shirt and medal.

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..

A Veterans Day running event in Dunedin on November 8, 2026 offering 5K, 10K and kids dashes along the paved Pinellas Trail with American themed finisher medals and family friendly kid runs.

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..

Take on the Colt 45 Trail Race at Colt Creek State Park with four looped distances from a 14 mile loop to an epic 60 mile challenge. Aid stations, GPS files, handcrafted medals and a post race picnic create a welcoming trail festival.

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.

This December relay race unfolds over two days at Alafia River State Park near Tampa. Teams of 8, 4, or 3 runners tackle scenic trails through shaded forests and sandy Floridian terrain. After their runs, participants gather in a festive vi..

Caloosa Fest in Alva, Florida features a Half Marathon and 5K on the Caloosahatchee Regional Park mountain bike trails, with on-course aid, vendors, awards, and packet pickup options.

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.