Trail Running calendar near Osprey 2025-2026

Run 10 miles over scenic nature and single lane mountain bike trails in Alva at Caloosahatchee Regional Park on January 4, 2026. Limited to 350 runners, the community race benefits local clubs and youth programs and includes a finisher shir..

Test your limits at the Long Haul 100 in Colt Creek State Park in Lakeland FL with a six loop 100 mile race or a 100 Furlongs loop. This Western States qualifier awards buckles and WSER lottery entry for finishes under 30 hours.

Join the Scrub Jay Races at Oscar Scherer State Park for scenic 5K and Scramble 10K courses, with virtual entries available through January. All finishers earn medals and support Florida scrub jay conservation.

Run a scenic trail through Harns Marsh with marsh lined paths and bird watching opportunities in this family friendly 5K and 1 Mile event. Held alongside the Wings Over Water festival, it pairs racing with outdoor fun and local vendors.

Travel back in time at the Time Travel Half Marathon in Fort Myers with half marathon, 10k, 5k, 1 mile and kids dash options. Celebrate with custom shirts and medals, chip timing, free photos and virtual or volunteer then run choices.

Take on the trails at Carlton Preserve in Venice for the second annual Coo Wah Chobee, a single loop trail run with distances from 50k to a 5k plus a youth 5k. Enjoy mixed single track terrain, signature swag and Wicked Skin awards.

Join the Pine Island Calusa Trail 5K on January 31, 2026 in Bokeelia, Florida for a scenic yet rugged trail run with solo, family and parent child entry options. Medals, post race refreshments and proceeds support Kiwanis youth programs.

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.

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..

Run the Gopherdillo Trail at Lake Manatee State Park in Bradenton on February 7, 2026 with scenic 5K and 10K courses over sand, grass and lakeside views. All finishers receive a medal and registration includes park entry.

Run the Hunt for Sasquatch at Bone Valley ATV Park in Mulberry on Feb 7, 2026. Choose 10K, 5K, a color 1 mile or multi distance challenges, enjoy rugged trails and small hills, collect swag and celebrate at the finish line awards party.

Sasquatch invites runners to Carlton Preserve in Venice Florida for 15k, 10k, 5k and a virtual race on Feb 15 2026. Expect race shirts, snacks, live music, vendor booths and a guided group stretch for all abilities.

Run the Downtown Dunedin Mardi Gras Runs Feb 15, 2026, with 5K, 10K, or 15K on the flat Pinellas Trail from HOB Brewing. Finishers receive a medal and tee and 21+ runners get a complimentary beer on a dog and stroller friendly course.

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.

All Day at Holloway in Lakeland Florida on Feb 28 invites runners to tackle a fast, well groomed 10k loop used for NCAA Division II regionals. Choose from 10k, 30k, 50k or a five person 50k relay for a lively community race day.

Celebrate St Patrick in Tampa on March 21, 2026 at the Time to Paddy 5k 10k and Lucky 13.1, featuring races from a kid's dash and mile to a half marathon. Enjoy festive shirts, finisher medals, chip timing and virtual options.

Run through scenic Colt Creek State Park in Lakeland on April 11, 2026 with 5K, 10K and half marathon options. Chip timed races include finisher medallions, swag and post race snacks for a fun day on the trails.

Join the fifth annual Turtle Trot at SunWest Park for 10K and 5K run or walk around scenic paved trails. Honor a fallen parks staff member and support Pasco County's adaptive programs while earning a finisher award.