Trail Running calendar near Kissimmee 2025-2026

Join the Little Big Water River 5K Trail Run and 1 mile stroll in Dade City, Florida on December 6, 2025 for a scenic true trail challenge. All finishers earn a medal and the day features a cookout with proceeds helping a new local church c..

Enjoy a festive Jingle Bell Dash 5K in Spring Hill on December 6 with a scenic cross country route at Bishop McLaughlin. Proceeds help build a new track and early registrants get a free race tee while top finishers receive holiday gifts.

Join RunFluent Christmas in Lutz FL on Dec 13, 2025 for a festive day of running with a 4 miler, 7 hour multi lap and 7 hour 2 person relay on a spectator friendly looped course. Enjoy varied trail surfaces, a race shirt and finisher awards..

Celebrate the season at the Candy Cane Course in Tampa on December 13 with festive 1 Mile, 5k, 12k, kids dash and virtual options for the whole family. Timed 5k and 12k races include finisher medals, shirts, free photos and Toys for Tots do..

Run scenic single loop trails through old growth forest, oak hammocks and salt marshes at the Trail Running Festival in New Smyrna Beach. Choose 12K, 24K or the epic 48K, with aid stations, a finisher medal and post race food.

Preview the 2026 LH100 course with a training run at Colt Creek State Park in Lakeland, FL on Dec 13, 2025. Run a marked 16.8 mile loop with water stops and day use facilities nearby. Registration closes Dec 12.

Join the Candy Cane Course at Waterfront Park in Clermont for festive races the whole family will love, from a family friendly 1 Mile and Kids Dash to timed 5k and 12k. Virtual and volunteer then run options add flexibility and holiday fun.

Join the festive Candy Cane Course in Clermont on Dec 14, 2025, with a 1 mile, kids dash, 5k, 12k and a virtual option for all abilities. Expect shirts, medals, chip timing, finish line treats and a Toys for Tots toy drive.

Peace River 100 Miler in Bartow, Florida scheduled for Dec 20, 2025 is cancelled. The race was set to challenge runners on looped grass and sandy trails with generous aid station fare and a 36 hour cutoff for the 100 mile distance.

Run shaded loops through Wekiwa Springs in Apopka, Florida on Jan 3 and 4, 2026 with 12 hour and 24 hour solo races plus a 24 hour team relay. Enjoy scenic trails, wildlife sightings and a lively runner village with campfires and shared cab..

Croom Zoom in Brooksville, FL invites you to run shaded trails through oak hammocks in Withlacoochee State Forest, with 50K, 20 mile and 10 mile options. The looped course keeps aid stations and drop bags within reach for a great day on the..

Join the Time Travel Half Marathon in Tampa on Jan 11, 2026 with 5k, 10k, 1 mile and kids races plus virtual entries. In person runners enjoy a designer shirt, custom medal, chip timing and free photos for a lively finish line.

Tackle scenic Florida trails at Long Haul 100 in Colt Creek State Park, Lakeland. Choose the epic 100 mile challenge or a shorter 12.5 mile loop and enjoy wildlife, aid stations and a finisher buckle.

Run through time in Orlando at the Time Travel Half Marathon with 5K, 10K, half marathon, 1 mile and kids races, available in person or virtually. Timed distances feature chip timing, custom bib, designer shirt, finisher medal, free photos..

Take on scenic Volusia County trails on Jan 24, 2026 with 50 mile, 50K and 17K options starting or finishing at Central 28 Beer Company in DeBary Florida. Enjoy trail views, on course aid, postrace food and a beer to celebrate your finish.

Run a relaxed, chip timed 5k through the vines at Masaryk Winery with wine themed swag and a post race pour. The grassy dirt course favors walkers and social runners over fast times.

Forgotten Florida by Run Bum Races is a weekend of trail runs in Christmas, Florida on Jan 31 and Feb 1, 2026, offering distances from 8 to 100 miles. Courses wind through palm groves, pine flatwoods and wetlands with chances to spot herons..

Join The Couple Shuffle in Tampa on January 31, 2026 for a festive couples friendly race offering a Kid's Dash, 2 Mile, timed 5k, 10k and 15K plus a virtual option. Expect shirts, medals, chip timing and age group awards.

Run the Ranch 5K in Sebring FL on Jan 31, 2026 invites runners and families to a scenic light trail course. Support Highlands County scholarships while racing at any pace and competing for age group medals.

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..