Trail Running Calendar Florida 2025-2026

This ain't your Mothers 50k & Trail Marathon is an annual trail running event held in Middleburg, Florida, within the scenic Jennings State Forest near Jacksonville. The race features multiple distances including a 50K, trail marathon, 12K,..

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.

Run the second annual Coo Wah Chobee at Carlton Preserve in Venice, FL on Jan 31, 2026 over scenic single track and double track trails with 50k, 25k, 5k and youth 5k options. Enjoy signature swag and Wicked Skin awards from RunFluent.

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..

Lace up for the Pine Island Calusa Trail 5K Run and Walk in Bokeelia on January 31 2026, a family and pet friendly outing that blends scenic Calusa Heritage Trail views with quiet neighborhood streets. Proceeds benefit the Kiwanis Club of G..

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 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.

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.

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.

Run with your pup at Wagging Tails on the Trails for scenic 5K and 9K routes, a Kids Puppy Dash and a virtual 5K. Proceeds support the St Lucie County Sheriff K9 unit and finishers get shirts and 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..

Hit the scenic trails at Lake Manatee State Park on Feb 7, 2026 for the Gopherdillo Trail Run, with 5K and 10K routes that showcase lake views and local wildlife. All finishers receive a medal and both distances follow separate no loop cour..

Hunt for Sasquatch at Bone Valley ATV Park in Mulberry for a playful trail race with a chance to spot Sasquatch. Choose a 1 mile color fun run, 5K, 10K or multi race challenges and enjoy a t shirt, swag bag and awards.

Run under the stars at Colt Creek State Park with a 5K, 10K, or the 15K Nighthawk Challenge combining both. Rugged trails, headlamp required, finisher medals and post race snacks for all finishers.

Experience the Sombrero Ultra Running Festival in Middleburg FL with races from 3 to 48 hours, live music, vendors, and themed giveaways. Bring your crew and enjoy a runner village, a single aid station, medical support, and awards.

Run Skunk Ape's Revenge in Green Swamp, FL on Feb 14 with 60K, 30K and 30K Ruck options across sand, single track and rolling berms. Enjoy frequent aid stations, finisher hats, overall awards and support a pet food drive for Cindy's Pets.

Take on the trails in Venice Florida at Carlton Reserve for Sasquatch on February 15, 2026, with 15k, 10k, 5k and a virtual option. Expect music, local vendors, a guided group stretch, a race shirt and post race snacks after a scenic run.

Explore scenic Lake Apopka from Magnolia Park on Feb 15, 2026 with 30K, 8 mile, 5K or virtual options for runners, walkers and cyclists. Trail terrain, tech shirt, finisher medal and post race food await.

Family friendly trail run at Disney Wilderness Preserve in Kissimmee with 5K, 10K or Double Down options and a Gopher Tortoise Fun Run for kids. Hats and finisher medals provided; the race is untimed and cupless so bring hydration.

Run the Space Pirate 100 along Florida Space and Treasure Coasts from Cape Canaveral to Jensen Beach; choose the 100 Miler, 100 Miler 3 person relay, 50 Miler or 33.3 Miler. Field is capped at 100, support crew only, and finishers earn a bu..