Trail Running calendar near Englewood 2025-2026

Take on a self guided 100 mile urban ultramarathon from Ybor City to Vinoy Park, tracing Tampa Bay’s coast through beaches and neighborhoods. Mostly flat with aid stations, finishers earn a 100 mile belt buckle and race swag.

Celebrate Veterans Day at the Dunedin Veterans Day 5K, 10K and Kids Dash in downtown Dunedin, a scenic out and back along the Pinellas Trail with American themed finisher medals for all. Family friendly with shirts for 5K and 10K runners an..

Take on the Colt 45 Trail Race at Colt Creek State Park on November 22, 2025, with distances ranging from 14 miles to a full 60 mile challenge. Run scenic looped trails past wildlife, enjoy stocked aid stations, handcrafted finisher awards..

Celebrate Thanksgiving with a family friendly Turkey Trails run at South County Regional Park in Fort Myers. Choose a Kids Dash, 1 Mile, 5k, 10k or go virtual and enjoy shirts, medals, free finish line photos and post race treats.

Run the scenic 60K Legacy Trail Ultra in Sarasota, starting and finishing at Payne Park along a mostly flat out and back route. Free to enter with limited aid and a 10 hour cutoff, this friendly club race welcomes solo runners and small rel..

Join Turkey Trails in Tampa on November 23 for a fun Thanksgiving run with distances for all ages: 1 Mile, 5k, 10k, Kids Dash and Virtual options. Chip timing, shirts, medals, free photos and post race refreshments make it a festive day.

Join the 14th annual FGCU Gobbler on Thanksgiving at FGCU Alico Arena for a festive 5K, 1 mile, or Tot Trot to support FGCU Cross Country. Fun for the whole family with a campus course, awards, and donation options.

Lace up for a festive Turkey Day 5K along the scenic Upper Tampa Bay Trail in Tampa. Enjoy chip timing, a turkey finisher medal, a comfy race shirt and postrace photos while soaking up holiday vibes.

Hit the scenic trails of Venice, Florida at the Trail Hog Half Marathon on November 29, 2025. Choose from a half, 10k or 5k and enjoy race shirts, post race snacks, music, vendor booths and age group awards.

Join the second annual Salty Soul Splash Dash, a festive 5 km fun run through Dunedin along the Pinellas Trail. Enjoy a timed finish, a race shirt and celebrate afterward with Salty Soul Island Kitchen.

Join Caloosa Fest Ultra in Alva, FL on December 6, 2025 for trail runs of 5K, 25K and 50K on a scenic loop of rolling hills and technical singletrack. Festival atmosphere, stocked aid stations and cupless racing make for a memorable day.

Run the Caloosa Fest 5K at Caloosahatchee Regional Park in Alva for a festival of trails, vendors and demos. Enjoy a scenic 5K, finisher medal and awards for the top three men and women in both morning and nighttime races.

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..

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.

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 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.

Celebrate the season at the Candy Cane Course in Punta Gorda on December 28, 2025 with family friendly options from a Kids Dash to chip timed 5k and 12k, plus virtual and volunteer then run entries. Free photos, medals and a Toys for Tots d..

Tackle a scenic 10 mile trail run at Caloosahatchee Regional Park in Alva, FL, weaving wide nature paths and single track through Florida woodlands. Limited to 350 runners with finisher shirt and pig logo tumbler, so register early.

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.