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Operation Outdoor Freedom Event

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.

Date
October 18, 2026 (87 days to go)
Price
$40–$55
Sports
Trail RunningRuckingRunning
Register →

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

5 Mile Ruck$40
5 Mile Trail Run$45
10 Mile Trail Run$55

Weather

Typical Conditions

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.

Sunrise 7:31 AMSunset 6:53 PMDaylight 11h 22m

Host City

About Middleburg, FL

Nearest Airport

JAX

Jacksonville International Airport · 30 mi

Time Zone

Eastern Time

From Endurance Grid

Line up lodging and travel early to lock in your race weekend.

Race Location

Your Next Start Line

What Are You
Waiting For?

Every finish line starts with a single decision. Claim your spot at Operation Outdoor Freedom Event, put it on the calendar, and turn “someday” into a start date.

87

Days to train

Race
Operation Outdoor Freedom Event
Date
October 18, 2026

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From Endurance Grid

About These Sports

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.

Trail Running

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.

Rucking

Covering a distance on foot under a weighted rucksack — from timed solo challenges to longer team events.

Running

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.

Plan your trip

Make it a Racecation

Coming from out of town? There's more to Middleburg than race day. We'll help you line up nearby lodging, flights, a rental car, and things to do so you can make the most of your racecation.

Plan your trip to Middleburg
Lodging
Flights
Rental Car
Activities

Frequently Asked Questions (FAQs)

What is the Operation Outdoor Freedom Event?+
Operation Outdoor Freedom Event is a trail running, rucking, and running race held in Middleburg, Florida on October 18, 2026. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more trail running races near you or explore our sports guides to learn what race day actually feels like.
When and where is the Operation Outdoor Freedom Event?+
Sunday, October 18, 2026 in Middleburg, Florida at Jennings State Forest Pioneer Trail. Check the event page for exact start times and wave schedules.
How do I register for the Operation Outdoor Freedom Event?+
Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.

Operation Outdoor Freedom Event

Oct 18, 2026

Register →