Trail Running calendar near Pensacola 2026-2027

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 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.

Run a scenic 50k on sand from Fort Morgan to the Florida state line near Flora Bama, tracing Alabama coastline and crossing two enforced bridges. Registration is postponed while organizers resolve permits.

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.

Trail half marathon and 5K at Krul Lake in Milton, Florida on November 14, 2026. The courses run through long-leaf pines and the event includes post race awards and a family friendly party with Hot Spot BBQ.