Trail Running calendar near Holiday 2026-2027

Holiday-themed races at Gadsden Park in Tampa on December 27, 2026, with distances from a kids 50 m dash to 15K, plus a virtual option, chip-timing, shirts, medals, photos, and finish-line treats.

A 100-mile ultramarathon and a 100 furlongs (12.5 mi) event at Colt Creek State Park on January 16–17, 2027, run as six 16.8 mile loops with three staffed aid stations and loop-by-loop drop bag access.

A chip timed 5 km run and walk at Masaryk Winery in Masaryktown, Florida on January 16, 2027, with a helper registration option, race items including a t-shirt and wine glass, and results posted online by J3 Timing.

Trail and road races at Oscar Scherer State Park include a 5K and a technical 10K plus virtual 5K and 10K options. Registration includes a finisher medal and a race shirt while supplies last.

Single loop trail races of 50k, 25k, 5k and a Youth 5k at Carlton Preserve in Venice FL on January 30 2027, organized by RunFluent. Registration is on UltraSignup and closes January 28.

A 12-hour, donation-supported trail run at Whispering Pines Park featuring a marked 5-mile loop through shaded single- and double-track trails. Participants may complete as many laps as they wish and receive an award after two loops.

A trail event at Lake Manatee State Park on February 6, 2027 with 5K and 10K courses through dirt paths, sand and pine corridors. The race features chip timing, finisher medals, post race snacks and age group awards.

Trail races at Bone Valley ATV Park include a 10K, 5K, and a 1 mile color run on hilly, uneven trails. Back to back challenge options require an 18 minute per mile pace and awards are given by age category.

Nighttime trail running at Colt Creek State Park with looped unpaved courses offering a 5K, a 10K, and a combined 15K challenge. 5K starters must use a headlamp and virtual entries receive mailed race items.

Experience a scenic trail race through the Carlton Reserve in Venice with distances ranging from 5k to 15k. Enjoy post race snacks and unique handmade wood awards in a festive community atmosphere.

Experience a unique single loop trail run through the Withlacoochee State Forest featuring 33 1/3 mile, half marathon, and 6K distances. Enjoy riverside trails and celebrate your finish with a post race barbecue and handcrafted medals.

Turtle Trot is a 5K run and walk at SunWest Park in Hudson, Florida, with a paved course around old salt mines. Proceeds support Pasco County's PAIR program and every registered participant receives a finisher award.

A backyard ultra at Lake Louisa State Park on April 10, 2027 where runners complete a 4.167 mile loop each hour until they can no longer start a loop; shirts, medals, ribbon sliders, and multiple award categories are offered.

Trail races at Colt Creek State Park on April 17, 2027 include 5K, 10K and a Half Marathon on flat, runnable pine forest trails. Events use chip timing and offer finisher medals, aid stations, and team awards.

Trail races of 10k, 30k and 50k take place at Loyce E. Harpe Park on April 17, 2027. The 10k loop repeats for longer distances on sandy, rolling mountain bike trails with aid stations and limited field size.

Trail marathon, half marathon, and 10K on unpaved Withlacoochee State Forest trails with three aid stations and mandatory personal hydration; primitive camping is available near the course.

A 5 km Stadion obstacle race at Raymond James Stadium featuring 20 obstacles, stadium stairs, and course elements like the Buccaneer bleachers, pirate ship, and animatronic parrot. A kids race and spectator access are also available.

Stomp Out Suicide is a shaded trail run and walk at Withlacoochee River Park on May 15, 2027, offering 10K, 5K and 1 mile distances and focusing on raising awareness about suicide; participants receive shirts, snacks, and finisher awards.

A trail race in Inverness FL on May 23, 2027 offering 50K, 25K and 10 mile single-loop courses through the Citrus Tract. Aid stations, drop bag service, and a post-race picnic are provided; runners must carry personal hydration.