Operation Outdoor Freedom Trailfest

Santa Rosa Beach, United States • 13 Sep 2025

Operation Outdoor Freedom Trailfest is a trail running event held in Santa Rosa Beach, Florida, starting at the Eastern Lake Trailhead off Hwy 395. Scheduled for September 13, 2025, the event offers three distances: approximately 5K, 10K, and 10 miles. The courses utilize well-marked forest trails, including yellow, red, and orange loops, providing a scenic and challenging experience.

The race supports Operation Outdoor Freedom, an organization offering recreational opportunities for wounded veterans. Participants receive a race shirt and finisher medal, with awards for overall and age group winners. Packet pickup is available the day before the race, and the event emphasizes a respectful refund policy due to weather uncertainties. Visit the organization's website for the most recent information.

Race information

10 mi
10 Miles (ish)
10 km
10k (ish)
5 km
5k (ish)
Visit the organization's website for the most recent information.
Trail runs nearby

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.

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.

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.