Trail Running Calendar Florida 2026-2027

Take on the Miami 100 on September 26, 2026, an open road 100 mile ultramarathon through iconic Miami neighborhoods. Limited to 50 runners, it leans on crew support and checkpoints and includes an optional 130 mile challenge.

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.

A community 5K, 10K and one mile event along the LaVilla Link and S Line Rail Trail in Jacksonville. Proceeds support Groundwork Jacksonville and local creek restoration and trail-building efforts.

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..

Join the PawPals 4 Life 5k on October 24, 2026 at Rock Springs Run State Reserve for an in person or virtual run that welcomes dogs and supports Pawfields Enrichment Group. Enjoy trail scenery, race swag, and medals for finishers.

Gate2Gate Trail Run offers 25k or 50k through single track, open fields, and rolling hills at San Felasco Hammock Preserve State Park on Oct 24, 2026. Enjoy aid stations, a finisher glass and medal, and support Friends of San Felasco.

The Greenway Trick 'R Trot will take place in Dunnellon on Saturday 24 October 2026. You can run between 5 and 10 kilometers.

Run hammock shaded single track just steps from the Atlantic at The Jacks in Palm Coast FL on Oct 25, 2026. Choose 50K, 24K or 12K loops in a field limited to 125, then cool off in ocean waters at the finish.

Join the Nightmare on the Clermont Trails 5K on October 31 in Clermont, Florida for a spooky run or virtual 5K featuring interactive spook zones, live actors, and a DJ. Dress up for the costume contest, snag the new 2026 finisher bling, and..

Experience the Wild Florida Trail Run along the Suwannee River in White Springs, Florida on November 7, 2026, with 50K, 25K and 10K options through oak and cypress lined trails. Proceeds benefit the Florida Trail Association.

Trail races at Lake Louisa State Park in Clermont offer 5K, 10K and half marathon routes through pine forests, lakeshores and meadows. Chip timed and welcoming to all, every finisher earns a medallion and age group prizes await.

Take on a 10 mile night trail at Jonathan Dickinson State Park with required headlamps and reflective course markings for a safe, scenic run. Dress up for the costume contest and enjoy a finisher medal, T shirt and a post race party with fo..

A community 5K at Vista View Park in Fort Lauderdale on November 7, 2026. Hosted by the Life Alliance Organ Recovery Agency, the evening run raises awareness for organ and tissue donation while honoring donors and recipients.

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.

Trail half marathon and 5K at Krul Lake in Milton, Florida on November 14, 2026. The courses run through long-leaf pines and the event includes post race awards and a family friendly party with Hot Spot BBQ.

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.

Run a scenic team relay through palm trees, giant ferns and sandy trails at Alafia River State Park near Tampa. Choose an 8 person standard team or 4 person ultra team for a two day, one night event with camping, music and bonfires.

Challenge yourself on scenic single track and rolling trails at Caloosa Fest with a 5K or Half Marathon through Caloosahatchee Regional Park. Enjoy on site vendors, gear demos, finisher medals and course support throughout the morning.

Timed 5K, 10K and 15K races start and finish at HOB Brewing Company in downtown Dunedin, combined with a holiday toy drive. The paved Pinellas Trail course is electronically timed and the event includes a finisher medal, event t shirt and a..

A 36.8 mile relay and ultra around Choctawhatchee Bay in the Destin area, traditionally held the last week of the year. The event features six unofficial legs, staggered starts for teams and an associated 5K recovery run.