Rule 62
Don't take yourself too seriously!!!
Events
S.O.S. - 09/06/2025
Fun in the sun!
Join us in the fun we will have at S.O.S., which could stand for Suffering On Sandridge, Service Over Self, or even $h!^ On a Shingle, on September 6th in the Jennings State Forest on the Sandridge Trail in Middleburg, Florida.
We will be offering 1 distance; 9K and 3 timeframes; 3,6,12 hours with each one will be run on an approximately 2.75 mile loop of the beautiful Sandridge Trail.
Wawa Crawl - 10/05/2025
2nd Annual WAWA Adventure Crawl!
We will take you on a 50k-ish journey or the newly added 20 miler to 5 Wawa's in the Middleburg, Orange Park, & Argyle Forest area ( Jacksonville, FL area).
This is NOT A RACE, it is an adventure event.
We will also give a portion of the proceeds to a local non profit Animal Rescue/ Shelter TBD.
Halloween havoc - 10/11/2025
Join us for a twilight/darkness trail running adventure on the majestic Pioneer Trail in Jennings State Forest for a unique one-of-a-kind trail race where we will be running right by Dunn Cemetery under the moonlit sky and glow sticks lining the trail! This is a 3.75-mile out-and-back course on a relatively flat course where at the 2-mile mark you will traverse through the historic Dunn Cemetery. We will have some exciting and exhilarating " features" along the route and will have a Halloween/Friday the 13th theme for all you superstitious and spooky type individuals!
Festivus 100 mile - 12/6/2025
Let’s get the holiday season started with the longest trail race in the Northeast Florida area! And if you guessed we are Seinfeld fans then you would be correct and our charismatic race director Russell Hartzell most definitely will have you “cracking up" with his one-liners and shenanigans!!
We like to have fun and follow the principles of Rule 62: Don’t take yourself too damn seriously!
This is the only 100 miler in NE FL.
Yo Momma - 01/25/2026
The 4th annual ( This ain't yo ) Momma's 50k & Trail Marathon, Sombrero Running Events likes to have fun and enjoy the beautiful scenery of this majestic trail here in NEFL. The Pioneer Trail IS NOT YOUR TYPICAL FLORIDA TRAIL, and the reason for that is each section has its own diverse style of terrain with Section 4 ( 2.7 miles ) having some of the most vertical and technical terrain you can find in Florida.
S.U.R.F. - 02/13/2026
2nd Annual WAWA Adventure Crawl!
We will take you on a 50k-ish journey or the newly added 20 miler to 5 Wawa's in the Middleburg, Orange Park, & Argyle Forest area ( Jacksonville, FL area).
This is NOT A RACE, it is an adventure event.
We will also give a portion of the proceeds to a local non profit Animal Rescue/ Shelter TBD.
Loopapolooza - 03/2026
LOOPAPALOOZA presented by Sombrero Running LLC you will be running/walking on a 1.2 mile paved loop 1/2 asphalt road 1/2 concrete walking path with a short "gravel" loop at the end, and surrounded by beautiful pine trees that nicely shade the course throughout the day for 3/ 6/ or 12 hrs. This a pancake flat and FAST course on a former active military base ( Cecil Field ).
OOF - 03/2026
Operation Outdoor Freedom provides recreational & rehabilitative opportunities to veterans on state forests, agricultural lands, & private lands throughout Florida @ no cost.
- Join us on Saturday, March 29th, 2025 in the Jennings State Forest on the Pioneer Trail for Operation Outdoor Freedom Event. We will be offering 2 distances; 5 & 10 mile (run & ruck).
MADRES fiesta - 05/9/2026
We are throwing a party for all of the Mom's out there to celebrate their day by having a Fiesta that will include Pinata's and the world-famous chorizo and egg burritos of the RD Mike Martinez of Sombrero Running Events LLC!
Come and join us on the beautiful Sandridge Trail in Middleburg, Fla for this annual event with distances of 1/2 Marathon, 14k and 7k as well as a 1-mile KIDS FUN RUN. These distances are on looped courses with the 1/2 marathon running a 6.65 mile loop 2x and 14k doing a 4.2 mile loop 2x and 7k = 1 loop of 4.2 miles on a flat-ish and non-technical and wide trail.
Who's Yo Daddy - 06/2026
Come and join!
Father's Day weekend event at the Oakleaf Community Park at 3979 Plantation Oaks Blvd for a 10k competitive run and 4k race The course is a 1.2 mile flat and fast loop course on a hybrid terrain of asphalt, compact sand, and a mix of grass and a short distance on a pine straw covered trail with the course being 75% shaded by trees to keep you cool.
Sombrero Sizzler - 07/2026
Welcome to the 2nd Annual Sombrero Sizzler presented by Sombrero Running LLC where you will be running/walking on a 1.25 mile paved loop 3/4 asphalt road 1/4 concrete walking path with a short "grassy" area at the end, and surrounded by beautiful pine trees that nicely shade the course throughout the day for 3/6/9/ or 12 hrs. There is also a Relay Team Option for the 6 race as well for 4 person teams of any gender (limit 10 teams). This a pancake flat and FAST course on a former active military base (Cecil Field). There will be plenty of fun and heat to go around.
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