Trail Running calendar near Holiday 2026-2027

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,..

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.

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 a trail running adventure through the pine forests and lakeshores of Lake Louisa State Park with Half Marathon, 10K, and 5K race options.

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..

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.

Hit the trails at the Carlton Reserve for the Sasquatch run. Choose from a 15k, 10k, or 5k race through the preserve. All finishers get a t-shirt and snacks, with unique handmade wood pieces for age group winners.