Trail Running calendar near Sarasota 2026-2027

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,..

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.

A veterans focused race in Tampa along the Courtney Campbell Trail offering 5K, 10K, half marathon and 15.5 mile courses with virtual options, aid stations, a military discount code, and post race gatherings at Whiskey Joes.

A trail race at Colt Creek State Park on November 21, 2026, offering four distances from 14 miles to 60 miles across repeated 14 mile loops. Aid stations serve each loop and finishers receive handcrafted awards.

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.

A trail event at Colt Creek State Park offering a 100 mile race and a 12.5 mile 100 Furlongs loop. The 100 Mile is a Western States qualifier with three staffed aid stations and finishers receive a belt buckle.