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!
Hotels Near This Race
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Race Travel Insurance
Don't forget travel insurance for October 18.
You've trained for months and booked a trip to Middleburg, FL.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is Operation Outdoor Freedom Event 2026 — Middleburg, FL?
Operation Outdoor Freedom Event 2026 — Middleburg, FL takes place on October 18, 2026. The race is held in Middleburg, Florida.
Where is Operation Outdoor Freedom Event 2026 — Middleburg, FL held?
Operation Outdoor Freedom Event 2026 — Middleburg, FL is held at Jennings State Forest Pioneer Trail in Middleburg, Florida.
Where can I find hotels near Operation Outdoor Freedom Event 2026 — Middleburg, FL?
RaceHotelFinder shows hotels sorted by distance from the race venue in Middleburg. Use the map or list view on this page to compare options and book race weekend accommodation.
