Trail Running calendar near University Park-South Downtown 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..

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.

Run a scenic 5k through Masaryk Winery vineyards with chip timing and a festive wine themed finish. Receive a tee, shatterproof collapsible wine glass and a finisher medal that doubles as a wine stopper while supporting Nik's Wish.

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.

A trail event at Green Swamp West Tract near Dade City offering 60K, 30K and a 30K ruck on varied Florida terrain with aid stations every 3 to 5 miles, finishers hats, and a local pet food drive.

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.

Join the inaugural Longleaf Blaze Trail Run at Disney Wilderness Preserve with 5K, 10K or Double Down options. Family friendly with kids activities, finisher medals and hats; bring your own water bottle and enjoy scenic trails.

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 scenic single loop trails along the Withlacoochee River in the Croom Tract with options from 6K to the challenging 33.3 mile distance. Enjoy aid stations, a post race picnic and a quirky vinyl record finisher award.

An annual St. Patrick's Day 5K and 10K in downtown Dunedin along the paved Pinellas Trail, featuring electronic timing, finisher medal, tech shirt, dog and stroller friendliness, and nearby parking and post-race activities.

Run the 30th Croom Fools Run in Withlacoochee State Forest near Brooksville, FL, with 16 mile, 50K and 50 mile options on a scenic 16 mile loop. Limited field and a laid back post race picnic make for a classic trail day.