Trail Running calendar near Osprey 2026-2027

Join the 26th annual Scrub Jay Races at Oscar Scherer State Park in Osprey, FL on January 24, 2026, with a fast 5K, a technical 10K trail scramble, and virtual options. Enjoy scenic courses, finisher medals, and proceeds supporting Friends..

Run the scenic Harns Marsh 5K on January 24, 2026 along marsh lined trails with wide open skies and great bird watching. All finishers get a commemorative medal and race shirt while a one mile fun run makes this a perfect family outing.

Travel through time at the Time Travel Half Marathon in Punta Gorda on Jan 24, 2026. Choose 5k, 10k, half marathon, mile or kids dash with chip timing, designer shirt, custom medal and free photos, plus a virtual option.

RunFluent's Coo Wah Chobee returns as a single loop trail run at Carlton Preserve in Venice FL, featuring mixed single and dual track trails. Distances from 50k to Youth 5k, plus 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.

A community 5K at Legacy Park in Venice, FL on January 31, 2026, with two age-based categories, chip timing, and post-race activities. Hosted by Respect 1st Responders to raise funds for Disaster Relief Kits; field limited to 200 runners.

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..

Join the Gopherdillo Trail Run at Lake Manatee State Park on Feb 7, 2026 for scenic 5K and 10K non loop courses over sand, grass and paved roads. Expect wildlife sightings, a performance shirt option, and a finisher medal.

Join The Hunt for Sasquatch at Bone Valley ATV Park on February 7, 2026 for a fun trail challenge over varied terrain and small hills. Choose from 10K, 5K, 1 Mile or multi race options, with shirts, swag and awards.

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.

Celebrate Mardi Gras on the flat, paved Pinellas Trail with 5K, 10K or 15K options hosted at HOB Brewing Company in Dunedin. Limited to 200 runners, all finishers get a medal and 21 plus registrants enjoy a complimentary beer.

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 offers a well groomed cross country loop of trail and road at Holloway Park in Lakeland on Feb 28, 2026. Choose 10k, 30k, 50k or a five person 50k relay.

Run through scenic Colt Creek State Park in Lakeland FL on April 11, 2026 with 5K, 10K, and half marathon distances. Trails, chip timing, a finisher medallion and post race snacks make this a lively spring event for runners and clubs.

Join the Turtle Trot 10K and 5K at SunWest Park on April 11 for scenic paved loops around old salt mines, perfect for runners and walkers. All finishers get awards and proceeds benefit Pasco Parks adaptive programs in memory of a staffer.

Join the Kraken road race in Sarasota on April 12, 2026 for a fun 5k or 10k along scenic routes. Enjoy race shirts, snacks, a finisher bottle opener, live music, vendors and age group awards for a festive Sunday run.

Run the Funest 50k at Carter Rd in Loyce E. Harpe Park, Mulberry FL. Choose 10k, 30k or 50k on a scenic 10k loop of sandy, rolling trails through old phosphate pits, limited to 100 runners for a fun, rugged challenge.

Run a scenic 5K through Lovers Key State Park on April 18, finishing by the Gulf of Mexico with chances to spot dolphins, shorebirds, and turtles. Proceeds benefit Friends of Lovers Key and park admission is included with registration.