Trail Running calendar near Holiday 2026-2027

A trail ultramarathon at Green Swamp near Dade City on February 14, 2026 offering 60K, 30K and a 30K ruck over varied Florida terrain, regular aid stations, a pet food drive and finisher hats.

Trail runs at Carlton Preserve in Venice on February 15, 2026 with 15k, 10k, 5k and a virtual race. The event includes a race t shirt, post race refreshments, music and age group awards.

Run through the restored wetlands of the Disney Wilderness Preserve on trails supporting over 1,000 species. This family friendly event features 5K, 10K, and Double Down distances. It's a cupless race with finisher medals and accessibility..

Run a flat, paved 15K on the Pinellas Trail during Dunedin's Mardi Gras festivities. This three-loop course is ideal for runners building distance. Enjoy a festive, themed event with a finisher's medal, T-shirt, and post-race beer.

A navigation-heavy, self-supported urban loop in Ocala featuring painted-horse artworks and two distance options. The untimed event emphasizes route-finding and sightseeing rather than racing.

An urban, self supported adventure run in Lakeland that follows a city route to view painted swan sculptures. The roughly 30k route emphasizes navigation, sightseeing, and a scavenger hunt atmosphere rather than competition.

Run a fast, groomed course at Holloway Park in Lakeland, FL, which hosts NCAA cross-country regionals. Choose from 10k, 30k, 50k, or a 5-person team relay.

A single loop trail event near Brooksville, Florida, offering 33.3 Miler, Half Marathon and 6K options with marked trails, aid for longer distances, finisher awards and a post-race picnic.

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.

The Croom Fools Run celebrates its 30th year with 50-mile, 50K, and 16-mile trail races on a scenic 16-mile loop in Florida's Withlacoochee State Forest. Runners enjoy a tech shirt, finisher awards, and a post-race picnic. The event is capp..

Trail races at Colt Creek State Park on April 11, 2026 offer 5K, 10K and half marathon on well marked wooded trails. Aid stations, on-course restrooms, chip timing, finisher medals and awards are provided.

Held at SunWest Park in Hudson, Florida, this event offers timed 10K and timed and untimed 5K options on a paved hiking path around old salt mines. Proceeds benefit the Pasco County PAIR inclusive programming and finisher awards are provide..

A 5K trail run and walk in Dunedin on April 11, 2026, that starts and finishes at Highlander Park and includes trails in Hammock Park. Kilts are encouraged and registration includes a T-shirt, medal, and Highland Games admission.

A community road race in Sarasota on April 12, 2026 offering 5k and 10k distances. The event includes race-day packet pickup, awards by age group, participant t-shirts and refreshments, and walk-ins are welcome.

Trail races on mountain bike trails at Loyce E. Harpe Park in Mulberry, FL offering 10k, 30k and 50k loop formats. The course features sand and dirt trails with rolling hills, limited entries, and a portion of fees supporting Polk County pa..

Run on the scenic trails of the Withlacoochee Forest, this event features marathon, half marathon, and 10K distances. Every finisher gets an award, and a festive post-race atmosphere awaits. Camping is available the night before at the prim..

Trail ultramarathon in Ocala, Florida with 50 and 100 mile options along the Florida National Scenic Trail, varied natural terrain, staffed aid stations, drop bag support, pacer rules for the 100 mile, and nearby campgrounds.

A shaded trail event at Withlacoochee River Park on May 2, 2026 offering 10K, 5K and 1 mile run or walk options. The race aims to raise awareness about youth suicide and includes shirts, snacks and finishers awards.

Trail races of 50K, 25K and 10 miles in Inverness, Florida on single-loop courses through the Citrus Tract of Withlacoochee State Forest. Aid and hydration stations are provided and runners must carry their own hydration.

An evening trail event at Croom Park in Brooksville with 21 mile, 14 mile, and 7 mile options on a 7 mile loop marked for night running with glow sticks. Headlamps are required and water stops are provided.