Operation Outdoor Freedom Event

  • Date Sun 18th October 2026
  • Time 8:00AM EDT
  • Location Middleburg, Florida
  • Price $44.90 - $60.80
  • Races 3 races
  • Distances 10 Mile, 5 Mile

Event summary

Get ready for an exhilarating day of outdoor adventure at the 4th Annual Operation Outdoor Freedom Event on Sunday, October 18th, 2026! Set in the picturesque Jennings State Forest in Middleburg, Clay, this exciting event offers two race distances: a 5-mile and a challenging 10-mile loop. Participants will navigate the stunning new Sawyer Trail, featuring the breathtaking Many Seeps Bridge, before tackling the rugged terrain of Section 4, renowned for its steep and technical challenges, and its scenic vistas overlooking Black Creek.

This cupless race encourages runners to bring their own hydration gear, ensuring a sustainable experience while enjoying well-stocked aid stations. With awards for all categories, including the coveted Slow A$$ award for the last-place finisher, every participant is celebrated! Plus, you'll receive custom dog tags as medals and enjoy a delicious spread of food and beverages at the finish line. Join us for a fantastic day of camaraderie and fun, all while supporting a worthy cause—100% of the proceeds benefit Operation Outdoor Freedom. Don’t miss out on this incredible opportunity to connect with nature and fellow outdoor enthusiasts!

Organiser's Description

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!

Races

  • 10 Mile Trail Run

    Incl. $5.80 Fee

    Sun 18th October 2026 (8:00AM EDT)

    $60.80

    OPENS TOMORROW
  • 5 Mile Trail Run

    Incl. $5.20 Fee

    Sun 18th October 2026 (8:00AM EDT)

    $50.20

    OPENS TOMORROW
  • 5 Mile Ruck

    Incl. $4.90 Fee

    Sun 18th October 2026 (8:00AM EDT)

    $44.90

    OPENS TOMORROW
    We adhere to the weight requirements of the Standard for male and females for Go ruck competitions, male 20lbs or greater, females 10 lbs or greater.

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Location

Jennings State Forest Pioneer Trail, 1335 Long Horn Road, Middleburg, 32068, FL, United States

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