Operation Outdoor Freedom Trailfest

Santa Rosa Beach, United States • 12 Sep 2026

Operation Outdoor Freedom Trailfest

Operation Outdoor Freedom Trailfest is a trail running event held on September 12, 2026, near Watercolor, Florida. The start line is at the Eastern Lake Trailhead off Highway 395. The event evolved from the Patriot's Run & Paddle, first held in 2020, and since 2025 it has partnered with Operation Outdoor Freedom.

Courses run on forest trails that are maintained and marked by the Forest Department; routes will also be marked on race day. Distances offered:

  • 5K follows the yellow loop
  • 10K follows the yellow perimeter, adds the red loop, then returns to yellow
  • 10 Mile follows yellow and red perimeters and adds the orange loop

All registered runners receive a shirt and a finishers medal. Runners registered by August 28 are guaranteed a shirt; late registrants may receive remaining shirts but are not guaranteed official race swag. Awards are given to 1st through 3rd overall male and female in each race, plus first place male and female in the listed age groups: 10-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70+.

Packet pickup is scheduled the day before at Fleet Feet Inlet Beach in Inlet Beach, Florida. The organizers will donate a portion of proceeds to Operation Outdoor Freedom. Rotorhead 30A Racing reserves the right to refuse any participant. If the event is cancelled due to weather, refunds will not be issued; runners may collect swag and medals at Fleet Feet Inlet Beach. Visit the organization's website for the most recent information.

Race information

10 mi
10miler
10 km
10k
5 km
Visit the organization's website for the most recent information.
Trail runs nearby

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The Grayt Jackalope 10 and 5 miler features two trail courses starting and finishing at Grayton Beach State Park, with awards for top finishers and age group winners and packet pick up the day before at Fleet Feet Inlet Beach.

A 36.8 mile relay and ultra around Choctawhatchee Bay in the Destin area, traditionally held the last week of the year. The event features six unofficial legs, staggered starts for teams and an associated 5K recovery run.

A 10 mile loop and a 20 mile two-lap trail race on January 23, 2027, through Pt Washington State Forest, featuring natural trail terrain, an official race hoodie for entrants, and awards by course and age group.

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