Events

05/10/2025

 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 Mariachi music and the world famous chorizo and egg burrito's of the race director Mike Martinez of Sombrero Running Events LLC! 

 Come and join us on the beautiful Sandridge Trail in Middleburg, Fla for this Inaugural 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.  

06/14/2025

Come and join us for this Inaugural Father's Day weekend event at the Oakleaf Community Park at 3979 Plantation Oaks Blvd for a 10k competitive run and 4k race (where the participants have to eat a cup of popcorn) at the start and 1/2 way point. 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. 

07/12/2025

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.

Join us in the fun we will have at S.O.S., which could stand for Suffering On Sandridge, Save Our Sombreros, Service Over Self, or even $h!^ On a Shingle, on Saturday, September 7th 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. There will be 1 well-stocked aid station at the start/finish and a hydration station. You will also have access to your vehicle and plenty of room for canopies and tents. This is also a cupless race so you must bring your own handheld water bottle or hydration vest and our aid station volunteers will fill it up for you.

10/18/2025

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! 

10/05/2025

2nd Annual  WAWA Adventure Crawl AKA WAC, where we will take you on a journey of a 50k ish distance or the newly added 20 miler to 5 Wawa's in the Middleburg, Orange Park, and Argyle Forest area ( Jacksonville Florida area). This is NOT A RACE it is an adventure event where you run from one Wawa to the next and are required to purchase an item from each store as your way of "checking in" and to support these local businesses. We will also give a portion of the proceeds to a local non profit Animal Rescue/ Shelter TBD. 

We also are doing this in a team format, where you need to partner up with at least one other runner ( it can be 1 or more other runners  but if you start together you have to finish together ), if you cant find a partner you can just team up with other runners at the race, so this way you can enjoy your journey together. This is strictly an Urban event and you MUST obey all traffic laws and can ONLY cross streets at intersections with a stop light or a stop sign.  

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 Mike Martinez most definitely will have you “cracking up" with his one-liners and megaphone shout-outs!! We like to have fun and follow the principles of Rule 62: Don’t take yourself too damn seriously! 

 01/26/2025

The 4th annual ( This ain't yo ) Momma's 50k & Trail Marathon has only 1 rule: Rule 62 = Don't take yourself so damn seriously!! Seriously though we at Sombrero Running Events like 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.

02/13/2026

Sombrero Ultra Running Festival

Registration is now OPEN!
We wanted to create a premier event that would bring runners from all over together to enjoy miles in NE Florida.  It was pivotal to that we allowed ample time for runners to reach their goals whether it is their first ultra, first 100-mile buckle or push themselves for more miles than they have ever done before.

Join us in Middleburg, Fl for a weekend full of fun with running, vendors, and other shenanigans.

03/23/2025

Welcome to the Inaugural 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 ). 

03/29/2025

Operation Outdoor Freedom provides recreational and rehabilitative opportunities to wounded veterans on state forests, agricultural lands, and private lands throughout Florida at 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 mile and 10 mile.

- JUST ADDED! This year we have the 5 mile ruck division.

- You will need to bring your own hydration vessel (handheld/ hydration pack) since we will once again be a CUPLESS RACE, we are environmentally conscious and this is a great way to maintain tha