Trail Running calendar near Holiday 2026-2027

Croom Zoom is a scenic trail run in Brooksville's Croom Park through oak hammocks and tree canopy, with 50K, 20 mile and 10 mile options. Entries cap at 250, so register by January 1, 2026 to secure your spot and chase a finisher award.

Test your limits at the Long Haul 100 in Colt Creek State Park in Lakeland FL with a six loop 100 mile race or a 100 Furlongs loop. This Western States qualifier awards buckles and WSER lottery entry for finishes under 30 hours.

Join the Scrub Jay Races at Oscar Scherer State Park for scenic 5K and Scramble 10K courses, with virtual entries available through January. All finishers earn medals and support Florida scrub jay conservation.

Join the Masaryk Wine Run 5K at Masaryk Winery for a scenic vineyard run with chip timed results and free race photos. Participants get a tee, shatterproof collapsible wine glass, a finisher medal that doubles as a bottle stopper and a pour..

Take on the trails at Carlton Preserve in Venice for the second annual Coo Wah Chobee, a single loop trail run with distances from 50k to a 5k plus a youth 5k. Enjoy mixed single track terrain, signature swag and Wicked Skin awards.

Run the Hero Dash 5K at Legacy Park in Venice, Florida to support Respect 1st Responders and help fund Disaster Relief Kits. Enjoy music, food trucks, vintage emergency vehicles and family fun after the race.

Celebrate the new year with Westly's 9th Annual 5K in Oakland, Florida. Run or walk the in person West Orange Trail event or join virtually anytime in January for a free, family friendly 5K with post race festivities and live music.

Celebrate Mardi Gras at Celery Fields with 5k, 10k and canicross races for runners and their dogs. Expect shirts, post race snacks, live music, vendors and age group awards plus a guided warm up.

Race under the stars at AdventHealth Nighthawk Trail Run in Colt Creek State Park with 5K, 10K and a 15K Challenge. Rugged unpaved loops, headlamp required for the 5K, finisher medals and a race shirt promise a memorable night on the trails..

Run the Gopherdillo Trail at Lake Manatee State Park in Bradenton on February 7, 2026 with scenic 5K and 10K courses over sand, grass and lakeside views. All finishers receive a medal and registration includes park entry.

Run the Hunt for Sasquatch at Bone Valley ATV Park in Mulberry on Feb 7, 2026. Choose 10K, 5K, a color 1 mile or multi distance challenges, enjoy rugged trails and small hills, collect swag and celebrate at the finish line awards party.

Run the Skunk Ape’s Revenge on February 14 in Dade City with 60K, 30K and a 30K Ruck across sandy single track, fire berms and dirt roads. Finishers get hats and stickers, top four men and women earn awards, and the race supports a pet food..

Sasquatch invites runners to Carlton Preserve in Venice Florida for 15k, 10k, 5k and a virtual race on Feb 15 2026. Expect race shirts, snacks, live music, vendor booths and a guided group stretch for all abilities.

Join the inaugural Longleaf Blaze Trail Run at Disney Wilderness Preserve in Kissimmee for scenic 5K and 10K trails through restored wetlands. Family oriented activities include a kids Gopher Tortoise Fun Run and finisher hats and medals.

Celebrate Mardi Gras on the flat, paved Pinellas Trail with 5K, 10K or 15K options hosted at HOB Brewing Company in Dunedin. Limited to 200 runners, all finishers get a medal and 21 plus registrants enjoy a complimentary beer.

Run through Ocala in the Painted Horse Urban Ultra, an untimed urban adventure and scavenger hunt with 55k and 25k loop courses visiting dozens of painted horse installations. Navigation heavy and mostly self supported.

Explore Lakeland on a 30k urban adventure visiting painted swans from the Swansation art trail while navigating with a race book. This low key, self supported run from the Where's the Finish? Podcast mixes city charm and relaxed challenge.

All Day at Holloway in Lakeland Florida on Feb 28 invites runners to tackle a fast, well groomed 10k loop used for NCAA Division II regionals. Choose from 10k, 30k, 50k or a five person 50k relay for a lively community race day.

Run single loop trails along the Withlacoochee River and through serene forest at the Long Play Trail Run in Brooksville. Choose from a 33.3 mile race, a half marathon or a 6K and earn a collectible vinyl record finisher award.

Celebrate St Patrick in Tampa on March 21, 2026 at the Time to Paddy 5k 10k and Lucky 13.1, featuring races from a kid's dash and mile to a half marathon. Enjoy festive shirts, finisher medals, chip timing and virtual options.