Trail Running calendar near Okaloosa Island 2025-2026

Join the Grayt Jackalope 10 mile and 5 mile on Saturday, November 22, 2025 in Inlet Beach at Grayton Beach State Park for scenic, sandy trail running with roots, rocks and coastal vibes. Staggered starts, age group prizes and a finisher awa..

Run the 15th Annual Round the Bay Relay and Ultra in Fort Walton Beach on December 27, 2025, choosing a scenic 36.8 mile solo ultra or relay teams of two to six. Circle Choctawhatchee Bay across bridges and hills with aid stations, live mus..

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.

Run the Ellie Biscuit Trail Trot in Santa Rosa Beach on Jan 24, 2026, offering 20 mile and 10 mile courses through the scenic Pt Washington State Forest. Expect rugged trails, roots, sand and mud for a true trail challenge.

In the Woods 30A 50K on Feb 21 2026 in Santa Rosa Beach challenges runners with 31 miles of sandy, rooty pine forest trails. Solo and 2 person or 3 person relays available, plus a trucker hat and finisher medal.

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..

Run the Bay to Breakfast 8K through scenic Big Lagoon State Park in Pensacola for a morning of trail miles and good company. Finishers enjoy pancakes and bacon at the Governor's Pavilion to refuel and celebrate.

Explore scenic trails and boardwalks at Panama City Beach Conservation Park in the Gulf Coast Conservation Trailfest, with 50K and 15K options on flat compact sand through cypress domes. Aid stations and post race food keep you fueled.

Take on a scenic 10 mile point to point trail run along Juniper Creek Trail on March 21, 2026. Run Pensacola provides aid stations, bus transport to the start and a finish at Blackwater State Park.