Trail Running calendar near Carrollwood 2025-2026

Run along the scenic Pinellas Trail from HOB Brewing in Dunedin with options of 5K, 10K or 15K while supporting a local toy drive. Finishers receive a medal, RUN FLORIDA shirt and a free draft for participants 21 and over.

Take on the Wekiwa Springs Ultra on Jan 3 to 4, 2026, choosing a 12 hour or 24 hour solo challenge or a 24 hour relay on a scenic 3.2 mile trail loop. Expect shaded paths, wildlife sightings, on course aid, and memorable finisher swag.

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..

Join the 26th annual Scrub Jay Races at Oscar Scherer State Park on January 24, 2026, offering in person 5K and 10K plus virtual options. Scenic trails, finishers receive medals, and proceeds support Florida scrub jay and park programs.

Run or walk a chip timed 5k through the scenic vineyards at Masaryk Winery, then enjoy a shatterproof wine glass and a wine pour for eligible participants. Proceeds benefit Nik's Wish and finishers receive a bottle stopper medal.

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.

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.

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..

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.

Sunset trail run at Colt Creek State Park in Lakeland FL on Feb 7, 2026 with 5K, 10K, or the Nighthawk 15K Challenge completing both races back to back. Expect unpaved terrain, headlamps required for the 5K, finisher medals and a race shirt..

Take on Skunk Ape’s Revenge at Green Swamp West by choosing 60K, 30K or a 30K Ruck and tackle sandy trails, single track and dirt roads through wild Florida scenery. Bring pet food for Cindy’s Pets and earn a finisher hat.

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.

Choose from 30K, 8 Mile, 5K or a virtual trail run, walk or bike along the scenic Lake Apopka trails starting at Magnolia Park. Enjoy lakeside views and birding, finisher medals and tech shirts, and remember the event is cupless so bring yo..

Join the 39th Real Florida 5K 10K at Wekiwa Springs State Park for a scenic off road run through natural Florida. Choose 5K or 10K, enjoy a capped field for a relaxed race vibe and a tech shirt and finisher medal for all entrants.

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.