Operation Outdoor Freedom Event 2026
- Date
- Sunday, October 18, 2026
- Start time
- 8:00 AM start (New York)
- Location
- Middleburg, Florida
- Entry fee
- From $55
- Fundraising
- Takes optional donations when you register
Registration is open.
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Events and entry fees
| Event | Distance | When | Entry fee | Cap |
|---|---|---|---|---|
| 10 Mile Ruck | 10 Mile | Oct 18, 20268:00 AM | $65 | 25 |
| 10 Mile Trail Run | 10 Mile | Oct 18, 20268:00 AM | $65 | 75 |
| 5 Mile Ruck | 8K | Oct 18, 20268:00 AM | $55 | 25 |
| 5 Mile Trail Run | 8K | Oct 18, 20268:00 AM | $55 | 75 |
Entry fees exclude processing fees. Prices and dates come from the race's registration page and refresh nightly.
Race day planning
Entry fee schedule
- 10 Mile Ruck and 10 Mile Trail Run: $65 until Oct 17.
- 5 Mile Ruck and 5 Mile Trail Run: $55 until Oct 17.
Online registration closes Oct 17, 2026, unless the race fills first.
How the price compares
At $65, entry is about the same as a typical 10-mile race in Florida ($65).
Light and altitude
Sunrise on race morning is at about 7:30 AM, and the 10 Mile Ruck starts at 8:00 AM. The start sits about 40 feet above sea level.
Fees exclude processing fees. Comparisons use current entry fees and published results from races nearby.
Start location and course
Jennings State Forest Pioneer Trail, Middleburg, FL 32068
The pin marks the address the race lists, which is usually the start. The organizers have not shared a course map with us yet.
2025 results
All results (2 years)5 Mile Trail Run
10 Mile Trail Run
5 Mile Ruck
Aggregated from official results (Fraser Affordable Sports Timing) for Operation Outdoor Freedom Event. Individual finisher names are not stored here.
How fast do you need to be at Operation Outdoor Freedom Event?
At the 2025 5 Mile Trail Run, the fastest tenth finished in 1:07:16 or better, the top quarter in 1:11:00, and half the field in 1:20:44; the last tenth came in after 1:37:05.
At the 2025 10 Mile Trail Run, the fastest tenth finished in 1:18:54 or better, the top quarter in 1:29:45, and half the field in 1:52:29; the last tenth came in after 2:13:15.
At the 2025 5 Mile Ruck, the fastest tenth finished in 1:09:30 or better, the top quarter in 1:09:51, and half the field in 1:46:39; the last tenth came in after 2:02:01.
| Age | Women | Men |
|---|---|---|
| 20-29 | 1:14:32 | n/a |
Groups with fewer than five finishers are left out. Awards vary by race; check the race's rules.
What would my time get me?
Where a finish time would have placed in 2025.
Finishers by year
Up 7 percent since 2024.
All events combined, from official results.
Typical race-day weather
Around October 18 the day usually runs from 60°F at dawn to 80°F in the afternoon, with measurable rain on about 9% of days. Cold snaps dip to 51°F and hot years reach 84°F.
Based on 75 days within a week of the date over the last 5 years, from historical weather for the start area. Not a forecast.
Race details
- Where
- Jennings State Forest Pioneer Trail, Middleburg, FL 32068Map
- Course
- Trail
- Start elevation
- About 40 feet
- Donations
- Accepted when you register
- Distances
- 8K, 10 Mile
- Editions
- 2026 (Oct 18, 2026), 2025 (Mar 29, 2025), 2024 (Apr 13, 2024), 2023 (Apr 2, 2023)
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Quick answers
- When is Operation Outdoor Freedom Event?
- Sunday, October 18, 2026, starting at 8:00 AM.
- How much does it cost?
- Entry starts at $55 before processing fees.
- When does registration close?
- Online registration closes Oct 17, 2026, unless the race fills first.
- Is the entry fee high for Florida?
- At $65, entry is about the same as a typical 10-mile race in Florida ($65).
- Can I donate to a cause when I register?
- Yes. The registration form offers an optional donation, usually for the charity or nonprofit the race supports. The race's own page names the cause.
- What distances can I run?
- 8K, 10 Mile.
- How big is it, and how fast?
- In 2025, 31 runners finished the 5 Mile Trail Run; the median finish was 1:20:44 and the winner ran 1:00:48.
- Where does it start?
- Jennings State Forest Pioneer Trail, Middleburg, FL 32068.
From the organizers
Join us on Sunday, October 18th at the Jennings State Forest on the Majestic Pioneer Trail for the 4th Annual Operation Outdoor Freedom Event. We will be offering 2 distances a 5 mile and 10 mile which each being a single loop that will traverse the brand new Sawyer Trail and over the Stunning Many Seeps Bridge ( huge walkway / footbridge in the middle of the forest) onto the " 4 way " section where the 5 milers will finish with a flat and fast last mile, the 10 milers will then traverse Section 4 which has some of the steepest and most technical terrain you will find in Florida as well as a few vista points overlooking Black…