Trail Running calendar near Oakland 2026-2027

Explore the Juniper Wilderness on the Florida Trail with the Two Prairies Ultra. This free 50K and 30K event starts at Pat's Island Trailhead, offering a scenic out-and-back course through the Ocala National Forest. Participation is limited..

Run or walk through the scenic orchards and vineyards of Formosa Winery in Kissimmee. Participants enjoy chip-timed results followed by cider and homemade donuts at this unique venue near Walt Disney World.

Join the festive St. Patrick's Day run in Dunedin on the flat, paved Pinellas Trail. Choose from a 5K or 10K course, both starting at HOB Brewing Company. The event includes a medal, tech shirt, and a post-race party in a family and pet-fri..

A kids' trail running series kicks off at Princess Place Preserve. Children race flat, dirt paths through the woods with distances by age group. Every finisher gets a wooden medal, and the event supports getting running shoes to kids in nee..

Trail runners take to the scenic paths of Silver Springs State Park in Florida for this event. Choose from a half marathon, 10K, or 5K on a beautiful course. Your race bib grants park access, and all finishers receive a tech shirt and medal..

Celebrate 30 years of trail running at the Croom Fools Run in Florida's Withlacoochee State Forest. Choose from a 50 miler, 50K, or 16 mile race on a scenic, looped course through pine forests and rolling hills. All finishers get an award,..

Run the trails at Colt Creek State Park on April 11, 2026. Choose from a 5K, 10K, or Half-Marathon distance. The event features chip timing, aid stations, and post-race awards.

The Turtle Trot 10K & 5K is a run/walk at SunWest Park in Hudson, Florida, on a paved path circling old salt mines. Every participant gets a finisher award, and proceeds support the PAIR program for inclusive recreation. T-shirts are availa..

Kick off the Dunedin Highland Games with this 5K trail run and walk. The scenic course starts and finishes at Highlander Park, venturing into Hammock Park. Registration includes a t-shirt, medal, and entry to the festival with Celtic music..

Join the fun at the DoNot Stop running event in Orlando, a donut-themed race with options from a kids dash to a half marathon. Every finisher gets a custom medal, event shirt, and a free donut. The event features chip timing and a virtual o..

Tackle the rolling hills and sandy trails of an old phosphate mine at the Funest 50K. This event offers 50K, 30K, and 10K distances on a challenging 10K loop course in Loyce E. Harpe Park. Runners can enjoy post-race food and support trail..

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..

Event Overview The Skunk Ape 100 Mile Endurance Run takes place on the Marjorie Harris Carr Cross Florida Greenway in Ocala, Florida. The course is a roughly 50-mile out-and-back route on the Florida National Scenic Trail and paved paths wi..

The Stomp Out Suicide Trail Race is a scenic event on May 2, 2026, in Dade City. It features a 10K, 5K, and 1-mile run/walk on shaded trails to raise awareness for suicide prevention. All participants get a shirt, snacks, and a finisher's a..

The Tick is a rugged 57.41-mile wilderness adventure on the Florida National Scenic Trail through Ocala National Forest. Crew support is mandatory for this point-to-point, no-frills ultramarathon. Participation is free but capped, with a su..

Turkey Creek 5K Trail Run takes place May 23, 2026 in Palm Bay at Turkey Creek Sanctuary. The event offers an on-site 5K and a virtual 5K with race shirts, medals for the first 300 registrants, finish-line refreshments and age-group awards.

Tackle a scenic single-loop trail course through Florida's Withlacoochee State Forest. Choose from a 50K, 25K, or 10-mile race, all starting and finishing at Holder Mine Campground. Expect full support, a post-race picnic, and a custom awar..

Run the trails of Croom Park at night in this unique evening event. Choose from three distances on a marked 7-mile loop. A headlamp is required to experience this nocturnal trail run.

Hit the trails for this unique summer event at Lake Louisa State Park. Choose between a 4-mile or 8-mile course and receive a leftover medal and swag. The race features live music, post-race refreshments, and awards.

The Independence Double offers a no-frills running experience over two days in Winter Park, Florida. Choose from five distances each day on a flat, shaded loop course. Expect a casual, hand-timed event with a focus on community and low entr..