Trail Running calendar near Okaloosa Island 2025-2026

Run a scenic 36.8 mile loop around Choctawhatchee Bay in Fort Walton Beach with solo ultra or team relay options. Expect aid stations, post race food and music plus a recovery 5K the next day.

Join Fred's Fight 5K in Lynn Haven on January 10 for an uplifting community run along the Rails to Trails pathway, with in person and virtual options. Proceeds help a local runner facing cancer and support their family.

Tackle sandy, rooty trails at Pt Washington State Forest near Santa Rosa Beach in the Ellie Biscuit 20 and 10 Mile Trail Race. Choose a 10 mile loop or double it for 20 miles for a scenic, challenging winter trail run.

Run the In the Woods 30A 50K at Point Washington State Forest near Santa Rosa Beach, a three lap trail challenge through sand, singletrack and creek crossings with two and three person relays. All entrants get a tech shirt and finishers rec..

Celebrate the 27th year of the Blackwater Heritage TrailBlazer on Feb 21, 2026 in Milton, Florida. Run a scenic, paved 13 km course or join the 2.7 mile fun run with strollers and leashed dogs welcome, then unwind at the brewery after party..

Join the Bay to Breakfast 8 km trail run at Big Lagoon State Park in Pensacola on February 28, 2026 for a scenic morning on the trails. Finish strong and enjoy a pancake and bacon breakfast at the Governor's Pavilion.

Run the scenic trails of Panama City Beach Conservation Park, winding over boardwalks through cypress domes and compact sand. Choose a 15K loop or tackle three loops for a 50K and enjoy post race food and aid stations.

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..