Trail Running calendar near Holiday 2025-2026

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.

Croom Zoom in Brooksville, FL invites you to run shaded trails through oak hammocks in Withlacoochee State Forest, with 50K, 20 mile and 10 mile options. The looped course keeps aid stations and drop bags within reach for a great day on the..

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.

Enjoy a scenic 5K through vineyards at Masaryk Winery on January 25, 2026, with chip timed results, a finisher medal, and a wine pour. This relaxed grassy course is made for a fun social run supporting Nik's Wish.

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.

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.

Explore shaded single and double track trails at Whispering Pines City Park on a scenic 5 mile loop that starts and ends at the pavilion. Free to join with donations welcome and complete 10 miles to earn a finisher award.

Run the wild trails of Green Swamp in Dade City with 60k, 30k, or 30k Ruck options over sand, single track and fire berms. Top finishers earn awards, all finishers get hats, and the race supports a pet food drive.

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.

Run Ocala's Painted Horse Urban Ultra, a low key, self supported navigation adventure from the Where's the Finish? Podcast on Feb 21 2026. Choose 55k or 25k loops that visit dozens of painted horses for a noncompetitive, unsupported adventu..

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 on Feb 28, 2026 invites runners to a scenic cross country style loop at Holloway Park in Lakeland, Florida. Choose from 10k, 30k, 50k and five person 50k relay on a well groomed course used in NCAA Division II regionals.

Run scenic single track through Withlacoochee State Forest along the river at the Long Play Trail Run in Brooksville, Florida. Choose 33.3 miles, a half marathon or 6K and finish with a vinyl record and post race picnic.

Celebrate the 30th annual Croom Fools Run on scenic trails through Withlacoochee State Forest, with 16 Mile, 50K, or 50 Mile loop courses, full aid stations, and a laid back post race picnic. Field is limited to 250 runners, so register ear..