
Operation Outdoor Freedom Event is a trail running, rucking, and running race on October 18, 2026 in Middleburg, FL, with entry fees from $40 to $55.
From the Organizer
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 Creek. There will be a well stocked aid stations at the 4 way section. This is also a cupless race so you will need to bring your own handheld water bottle or hydration vest and our aid station volunteers will fill it up for you. The Race Director for this race is Mike Martinez with Sombrero Running Events LLC, he is known for his only rule at the races that he directs and that is RULE 62: Dont take yourself too darn seriously. We will have OA awards for all distances as well as Masters Awards and Mike's coveted Slow A$$ award for those that finish in last place because we believe all runners/walkers are important!! We will also have custom made dog tags for medals for all participants and also have our usual spread of food and non alcoholic beverages ( the Florida Forest Service does not allow any alcoholic beverages on its property so please also respect this and refrain from bringing your own) If interested in sponsoring our event please contact Mike Martinez RD at mike42892@yahoo.com
100% of the proceeds will go directly back to Operation Outdoor Freedom!
Events
Weather
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
81°
Typical Low
65°
Chance of Rain
25%
Based on US Climate Normals data from Jacksonville Nas, 16 mi from the venue.
Host City
Nearest Airport
JAX
Jacksonville International Airport · 30 mi
Time Zone
Eastern Time
From Endurance Grid
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Race Location
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From Endurance Grid
This race spans more than one sport — here’s a guide to each, so you can understand what’s involved and decide if it’s the right fit. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.
Running off-road — dirt, singletrack, and mountain paths — from 5Ks to ultras. The terrain makes for an exciting twist and adventure in your running journey.
Covering a distance on foot under a weighted rucksack — from timed solo challenges to longer team events.
From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
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Plan your trip
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Operation Outdoor Freedom Event
Oct 18, 2026