Trail Running calendar near Osprey 2025-2026

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.

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 the scenic Harns Marsh 5K or family friendly 1 Mile on January 24, 2026, through marsh lined trails alive with birds. The race is part of the Wings Over Water festival with vendors and activities and benefits Unite Lehigh.

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.

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..

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.

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 on rugged trails at Colt Creek State Park with 5K, 10K and a back to back Nighthawk 15K Challenge. Expect sandy, rooty terrain, a commemorative shirt and medals, and bring a battery powered headlamp for the 5K.

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 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 invites runners to tackle a scenic mix of trail and road on a maintained 10k loop at Holloway Park in Lakeland, FL. Choose from 10k, 30k, 50k or a five person 50k relay and race a course used for collegiate competition.

Join a chip timed trail run at Colt Creek State Park in Lakeland FL on April 11, 2026, with 5K, 10K and half marathon options on well marked, family friendly trails. Finishers receive swag and a medallion and courses have aid stations.

Join the Turtle Trot at SunWest Park in Hudson on April 11, 2026, for scenic 5K and 10K runs along paved trails around former salt mines. Timed and untimed options, finisher awards for all, and proceeds benefit PAIR.

Dive into The Kraken in Sarasota on April 12, 2026 with 5k and 10k options for runners of all paces. Enjoy music, vendors, pre race group stretching, snacks, commemorative tee and a finishers bottle opener while awards honor top finishers.

Run the Funest 50k at Loyce E. Harpe Park in Mulberry with 50k, 30k, and 10k options over rolling sand and dirt trails. Entry is limited to 100 runners with aid, finisher swag, and funds supporting Polk County parks.

Enjoy scenic trail running through shaded woods and hammocks at Gator Wilderness Camp in Punta Gorda with 5k, 10k, 15k, a Kids Fun Dash and a virtual option. All entry proceeds support Gator Wilderness Camp School for adolescent boys.