Whispering Pines

John Holmes Trail Run takes place in Brooksville, Florida, at Croom Park within the Withlacoochee State Forest. Now in its 33rd running, this Southeast’s oldest 50K trail race began as the Croom Trail 50K and was renamed in 2006 to honor founder John Holmes. The challenging course runs along the Cro..

The Itch is a rugged, no-frills 50K trail race in Ocala, Florida, running along the Florida National Scenic Trail’s West Corridor. This point-to-point course travels from the East-West Junction to the Baseline Road Trailhead, winding through Florida’s wilderness with minimal amenities. Runners recei..

The Greenway Trick 'R Trot is a Halloween-themed trail race held at the Pruitt Trailhead in Dunnellon, Florida. Scheduled for October 25, 2025, the event offers multiple race options including 5K and 10K runs and rucks, as well as combined 5K+10K challenge races. Participants race through scenic tra..

Landbridge Trail 5k is a well-marked, 5-kilometer loop on the Florida Trail in Ocala, Florida. The course climbs to the top of the famed Landbridge in the Marjorie Harris Carr Cross Florida Greenway, following Blue and Orange blazed trails. Runners can race hard or slow to snap a photo at the Landbr..

Florida 48 – 4x4x48 Ultra Marathon takes place at Shangri-La Trailhead & Campground in Ocala, Florida. The event challenges participants to complete 4 miles every 4 hours over 48 hours, totaling 48 miles, on a non-technical out-and-back course. The route starts and returns to camp, featuring 0.75 mi..

Jingle Bell Dash 5K Run/Walk is set on the campus of Bishop McLaughlin Catholic High School in Spring Hill, Florida. The cross-country style course spans the school’s 88 acres and winds through fields, trails, and open pavement, welcoming runners and walkers of all levels. The event supports the dev..