Trail Running calendar near Okaloosa Island 2026-2027

Join Fred's Fight 5K in Lynn Haven to support a local family facing cancer. Run the scenic Rails to Trails route or take part virtually to help cover medical costs and show solidarity.

Run rugged trails at Point Washington State Forest with a 10 mile loop or a 20 mile two lap race from Eastern Lake Trailhead. Expect roots, sand and singletrack plus a finisher award and a hoodie for early registrants.

Tackle the rugged In the Woods 30A 50K in Santa Rosa Beach, FL, a three lap trail race over sandy paths, creek crossings and rooty singletrack. Solo runners and two or three person relays are welcome for a scenic, challenging seaside advent..

Run a scenic, tree lined paved trail in Milton at the Blackwater Heritage TrailBlazer. Choose a 13 km challenge or a 2.7 mile fun run with family friendly perks, post race vendors and an after party to celebrate every finish.

Join the Bay to Breakfast 8K Trail Run at Big Lagoon State Park in Pensacola on Feb 28, 2026. Enjoy scenic trails then refuel with a pancake and bacon breakfast at the Governor's Pavilion. Limited spots available.

Run scenic trails and boardwalks at Panama City Beach Conservation Park in the third annual Gulf Coast Conservation Trailfest, offering 15K and 50K loop options. Enjoy flat compact sand, on course aid, and a relaxed Florida trail vibe.

Run Pensacola's Blackwater 10 Mile Trail Run on March 21, 2026 is a point to point 10 mile route along the scenic Juniper Creek Trail finishing at Blackwater State Park. Finishers receive a medal and t shirt and aid stations will support yo..

The 5K for the Bays will take place in Inlet Beach on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

Wildcat Ultras in Pensacola on September 5, 2026 offers 15 to 100 mile races on a fast 2.5 mile loop through scenic parkland. Frequent crew access, stocked aid, chip timing and RV hookups make this a welcoming ultra weekend.