Trail Running calendar near Holiday 2026-2027

Single-loop trail races of 50K, 25K and 10 miles in the Citrus Tract of Withlacoochee State Forest near Inverness FL. Multiple aid and hydration stations, mandatory personal hydration, drop bag service, camping and a post-race picnic.

A twilight trail running event at the Santos trailhead in Ocala, Florida, organized with the Hump Day Hustle series. The course is about 2.8 miles and participants are required to wear a headlamp; shirts are available for purchase.

Evening trail running at Croom Park in Brooksville with 21 mile, 14 mile and 7 mile options. The marked 7 mile loop uses the B C Loop and C Loop; headlamps are required and glow sticks mark the course.

Treat Trot-Orlando in Minneola, FL on June 6, 2026 offers in-person and virtual options across Kids Dash, 1 Mile, 5K, 10K, 15K, plus a volunteer then run option. Registrations include a shirt, bib, medal, photos, and postrace snacks.

Join the Treat Trot at Gadsden Park in Tampa for a day of running with distances ranging from a Kids Dash to a 15K. Enjoy chip timed results, finisher medals, and free event photos in a scenic park setting.

Two trail races at Lake Louisa State Park offering 4 mile and 8 mile loop options, chip timing, aid stations, on course restroom, live music and post race refreshments. Throwback swag and age group awards are part of the event.

A community 5K at Robinson Preserve in Bradenton on June 13, 2026, with a $35 registration fee. Participants receive a t-shirt, snacks and hotdogs, and awards are given to the top three men and women in each age group.

An indoor, last-one-standing treadmill endurance event limited to 33 athletes; competitors run 5 miles each hour until only one remains, with a recovery zone, temperature control, rotating music, and limited spectator space.

A night trail race on July 18, 2026 in Green Swamp West Tract near Dade City, Florida. The 30K course mixes pasture lanes, singletrack, sand and berms, with aid stations every 3 to 5 miles and no cut-off time.

Summer Sizzler in Tampa on 08/01/2026 features timed 5K 10K and 15K races, untimed 1 mile and kids dash, and a virtual option. The event includes chip timing, shirts and medals, free photos and finish line treats.

Experience the Withlacoochee Forest after dark in this night trail race featuring 5, 10, and 20 mile distances. Navigate single track trails under the stars with glow stick markers and a post race picnic celebration.

An 8 hour timed trail event at Ross Prairie Trailhead in Dunnellon, Florida, featuring a 6.5 mile berm loop through longleaf pine, oak hammocks and dry prairies. Self crewing and nearby campground facilities are available.

The Pinellas Trail Challenge will take place in University Park-South Downtown on Saturday 5 September 2026. You can run 46 miles.

A night trail half-marathon in the Green Swamp West Tract near Dade City, Florida, with run and ruck options, a turnaround aid station, labeled drop bag support, ruck weight standards, and a post-race potluck.

Trail run at Central Florida Bible Camp in Eustis with a roughly 3.2 mile two loop option and a single loop fun option. Runners can attempt up to ten field day stations such as inflatable obstacles, axe throwing, and cornhole.

Tick Tock Ultra on September 19, 2026 is a timed ultrarunning event with 6 hour and 12 hour individual formats plus a 12 hour 5 person relay, organized by Ultra Ultras.

A timed lake lap event at Lake Hollingsworth in Lakeland, FL offering 12 hour, 6 hour and team relay options. Runners complete 2.84 mile laps on a paved walkway and the field is limited to 200 entrants.

Choose a 5 km or a two loop 10 km course from HOB Brewing Company along the Pinellas Trail. Stroller and dog friendly with electronic timing, finisher medals, and a free draft beer for participants aged 21 and over.

Join this local running event in Tampa featuring distances from a Kids Dash to a Half Marathon. Enjoy chip-timed results, pacers, and finisher medals for all participants in a family-friendly atmosphere.

The John Holmes Trail Run takes place at Croom Park and Withlacoochee State Forest on October 3, 2026, offering 50K, 16 mile and 9 mile options. The field is limited to 250 runners and this is the event's 34th running.