Operation Outdoor Freedom Trailfest

Operation Outdoor Freedom Trailfest : Santa Rosa Beach, FL

Operation Outdoor Freedom Trailfest is a trail running event held at the Eastern Lake Trailhead off Hwy 395 into Watercolor in Santa Rosa Beach, Florida on September 12, 2026. Distances offered include:

• 10 miles
• 10K
• 5K

Courses run on marked forest trails. The 5K follows the yellow loop; the 10K follows the outer yellow perimeter, connects to the red loop, then returns to the yellow loop to finish; the 10 miles course follows the outer yellow and red perimeters and includes the orange loop before returning to the finish. Trails are already marked by the Forest Department and will be marked on race day.

All registered participants receive a shirt and a finisher medal. Runners who register by August 28 are guaranteed a shirt; later registrants may receive remaining extras but shirts are not guaranteed. Awards include 1st through 3rd overall male and female in each race, plus 1st place male and female in standard age groups: 10-19, 20-29, 30-39, 40-49, 50-59, 60-69, and 70+.

Packet pick-up is scheduled for September 11, 2026, with an additional small pickup available the morning of the event. The listed packet pickup location is Fleet Feet Inlet Beach at 11299 US Hwy 98 E, Inlet Beach, FL.

The event’s refund policy states registration fees are non-refundable; transfers to another runner are allowed within the posted transfer period. Animals are not permitted in races. Strollers and wagons must start at the back of the pack. Rotorhead 30A Racing reserves the right to refuse any participant. Participants using certified running wheelchairs or adaptive devices should contact organizers in advance to arrange accommodations. Visit the organization's website for the most recent information.