Trail Running calendar near Okaloosa Island 2025-2026

Run a scenic half marathon through long leaf pine forests around Krul Lake in the Blackwater River State Forest on November 15, 2025. Celebrate at the finish with Hot Spot BBQ, awards, and a relaxed post race gathering hosted by Run Pensaco..

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..

Tackle the scenic 36.8 mile Round the Bay Relay and Ultra around Choctawhatchee Bay in Fort Walton Beach on December 27, 2025. Choose solo or team relays and enjoy aid stations, a beachfront host hotel and lively post race food and music.

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.

Take on Death by 5k Coldwater Creek a 24 hour challenge of ten 5k loops along scenic single track beside Coldwater Creek in Milton Florida. Camp, refuel and earn a handmade finisher coffin if you complete the day.

Punch Out Ultra is an 8 hour timed trail run in Molino, Florida where solo runners and four person teams loop 4.2 mile ATV style laps on rugged wooded trails. Earn medals or a limited Suffer Up 50K coin and enjoy aid and a free kids race.

Tackle sandy pine trails and creek crossings at In the Woods 30A 50K in Santa Rosa Beach. Run solo or as a two or three person relay and earn a finisher medal on scenic, technical forest singletrack.

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.