Trail Running Events & Ultramarathons | Sombrero Running

Trail Races & Ultramarathons

Inclusive, community-driven running events across Northeast Florida. From 5Ks to 100-Milers & 48-Hour endurance challenges.

📅 Sept 12, 2026

S.O.S.

📍 Location: Middleburg, FL
🏃 Distance: 3, 6, 12 hours +Ruck options

Join us in the fun we will be having 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 12th 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.

📅 Nov 7, 2026

Dunns Ultra Marathon Badasses

📍 Location: Pomona Park, FL - Dunns Creek State Park
🏃 Distance: 100 Miles / 100k / 35 Miles / 12 Miles / 8k / Ruck Options

That's right we are some Bada$$es! to tackle this awesome terrain at the beautiful Dunns Creek State Park in Pomona Park, Florida just south of Palatka. This trail system has just about everything a Florida trail offers, EXCEPT no swamp :) and while there might not be any gators lurking there is a bountiful of other wildlife you might get to experience. We at Sombrero Running Events like to explore and challenge ourselves mentally and physically as we experience TRAIL THERAPY and this awesome 11.90 mile ish looped course will challenge you as you traverse this diverse terrain. You will get to see the natural landscape consisting of longleaf pines, wiregrass and sandpine scrub that protects several endangered and threathened species such as the gopher tortoise, fox squirrel and other native animals.

📅 December 5, 2026

Festivus 100 Mile

📍 Location: Middleburg, FL
🏃 Distance: 35M / 50M / 100M

Kick off the holiday season with the longest trail race in Northeast Florida! Seinfeld-themed fun, Rule 62 principles, and pure trail endurance.

📅 January 2, 2027

Oceans 26.2 Marathon Relay

📍 Location: Atlantic Ocean Coast, NEFL
🏃 Distance: 26.2 Miles (Solo or Teams of 2-3)

A shaded 3-loop oceanfront course. Ruck or run with your crew, enjoy a centralized transition area, and breathe in the salt air.

📅 January 31, 2027

(This Ain't Yo) Momma's 50K

📍 Location: Pioneer Trail, Middleburg, FL
🏃 Distance: 50k, Trail Marathon, 12k & 7k

Annual trail challenge featuring diverse terrain and Section 4's technical Florida elevation gain.

📅 February 12, 2027

S.U.R.F. (Sombrero Ultra Running Festival)

📍 Location: Clay County Regional Sports Complex, Middleburg, FL
⏱️ Format: 6HR / 12HR / 24HR / 48HR Timed Event

Premier endurance event designed to give runners ample time to hit ultra milestones or earn their first 100-mile buckle.

📅 Mar 20, 2027

The Cow Ford

📍 Location: Jacksonville, FL
⏱️ Format: 100 Mile / 50 Mile

This event is an exploration of the city's history, waterways, and neighborhoods. The course is composed of five distinct segments, each with its own character and story, forming a continuous narrative from historic neighborhoods to the Urban Core finish. WHY JACKSONVILLE WAS CALLED "COWFORD"

📅 May 8, 2027

Madres Fiesta

📍 Location: Middleburg, FL
⏱️ Format: 13.1 Mile / Other shorter options

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 race director 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.

📅 July 2027

Sombrero Sizzler

📍 Location: Cecil Field, FL
⏱️ Format: 3 Hr / 6 Hr / 9 Hr / 12 Hr / Ruck Options

Welcome to the 4th Annual Sombrero Sizzler presented by Sombrero Running Events where you will be running/rucking 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.

Need Event Camping or Have Questions?

Check campsite availability for Festivus or reach out to Race Director Russell Hartzell.