Operation Outdoor Freedom Event

Operation Outdoor Freedom Event

Operation Outdoor Freedom takes place on October 18, 2026, at Jennings State Forest on the Pioneer Trail in Middleburg, FL. The event offers trail running and rucking on single-loop courses that use the new Sawyer Trail and cross the Many Seeps Bridge. The 10 mile route continues onto Section 4, which includes steeper and more technical terrain and several vista points overlooking Black Creek. The 5 mile route finishes at the 4 way section with a flat final mile.

Distances:

• 5 Mile Trail Run single loop, flat final mile
• 10 Mile Trail Run single loop, includes Section 4 vistas
• 5 Mile Ruck single loop, weight requirements apply for rucking
• 10 Mile Ruck single loop, weight requirements apply for rucking

There will be a well stocked aid station at the 4 way section. The event is cupless, so participants must carry their own hydration; volunteers will refill handheld bottles or hydration vests. Awards include overall and masters placements and a last-place award. All participants receive custom dog tag medals. Food and nonalcoholic beverages will be available on site; alcoholic beverages are not allowed on Florida Forest Service property. Registration opens in July and closes in September, with fees shown between $45 and $55. One hundred percent of proceeds are directed back to Operation Outdoor Freedom. Visit the organization's website for the most recent information.

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