Operation Outdoor Freedom Event
10 mi5 miRegistration open

Operation Outdoor Freedom Event

Middleburg, Florida200 spots
Entry from
$55
Days to go
12

At a glance

Date
Oct 18, 2026
Location
Middleburg, Florida
Distances
10 mi, 5 mi
Registration
Registration open until Oct 17, 2026, via runsignup.com
Official site
runsignup.com
Listed from
RunSignUp
Last checked
Oct 5, 2026

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About this race

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!

Key dates

Registration opens

Jul 24, 2026

Tier 1 ends

Sep 6, 2026

Tier 1 ends

Sep 7, 2026

Registration closes

Oct 17, 2026

11d

Tier 2 ends

Oct 17, 2026

11d

Race day

Oct 18, 2026

12d

Pricing

10 Mile Ruck

Tier 2, until Oct 17, 2026

$65

10 Mile Trail Run

Tier 2, until Oct 17, 2026

$65

5 Mile Ruck

Tier 2, until Oct 17, 2026

$55

5 Mile Trail Run

Tier 2, until Oct 17, 2026

$55

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Straight-line distance

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