Trail Running calendar near Osprey 2025-2026

Join PHSC cross country teams at Pasco Hernando State College for Run with the Bobcats, a flat, fast 5K and 1 mile Bobcat Trot on the Wellness Trail. All ages welcome, with race shirts and post race refreshments and proceeds supporting PHSC..

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.

The Dunedin Veterans Day 5K, 10K and Kids Dash Runs take place in downtown Dunedin, FL. The course starts and finishes near the VFW at the Dunedin Hale Center, 330 Douglas Avenue, and runners traverse the paved Pinellas Trail on a northboun..

Run the Colt 45 Trail Race at scenic Colt Creek State Park near Lakeland, Florida. Choose from four distances from a 14 mile loop to a 60 mile double loop and enjoy aid stations, unique finisher awards and a post race picnic.

Turkey Trails- Fort Myers, organized by Bodies Race Company, takes place at South County Regional Park in Punta Gorda, Florida. The Thanksgiving-themed event offers multiple distances—1 Mile, 5k, 10k—plus a Kids Dash, Volunteer-then-Run opt..

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.

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..

Turkey Day 5K Tampa Bay is a Thanksgiving-themed 5K run/walk held along the Upper Tampa Bay Trail in Tampa, Florida (near Citrus Park). The scenic, nice-down-and-back course follows the trail with a street crossing assisted by Hillsborough..

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.

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.

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 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..

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..

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.

The Downtown Dunedin Holiday 5K, 10K, and 15K With Toy Drive is held at HOB Brewing Company in downtown Dunedin, Florida. It offers three distances: a 5K, a 10K (two 5K loops), and a 15K (three 5K loops), all on a fully paved course along t..

Choose a 12 hour, 6 hour, 12 hour relay or 5 mile loop at scenic Lake Wailes on December 20, 2025. Field limited to 100, all entrants receive a long sleeve shirt and a lively runners village with hot grilled food.

Celebrate the season with the Candy Cane Course in Punta Gorda on December 28, 2025, featuring family friendly distances from a kids dash to 12k plus a virtual option. Enjoy festive swag, chip timing, and donate new toys for Toys For Tots.