Prepare for an unforgettable trail experience at "This ain't your Mothers 50k & Trail Marathon," set to challenge runners on January 25, 2026, in Middleburg, FL. This event, now in its fifth year, is hosted by Sombrero Running Events, known for its emphasis on fun and embracing the beautiful outdoors with the guiding principle: "Don't take yourself so damn seriously!". Runners can choose from distances including a 50K, Marathon, 12K, and 7K, all taking place entirely on un-paved trails within the scenic Jennings State Forest.

The Pioneer Trail, a hidden gem created in 2019, offers a surprisingly diverse and challenging course that defies typical Florida terrain. Expect mostly single track with a dynamic mix of vertical and technical sections, including the infamous "Mt. Reagan" and vistas overlooking the Black Creek Ravines. Runners will traverse through beautiful scenery featuring waterfalls and walkover stream crossings. Previous participants have described the course as "incredibly steep," with "constant up and down, with plank crossings, water, sand, rope handrails, rock," making for a truly demanding yet rewarding adventure. Typical race day conditions in late January are ideal, with highs around 66F and lows around 47F, and only a 10% chance of precipitation.

Aid stations, positioned approximately every 2.5 to 3 miles, will keep you fueled with water, electrolyte nutrition like Tailwind/Skratch, and standard ultra-distance fare. This is a cup-less race, so be sure to bring your own hydration system. The race fosters a supportive atmosphere, with past runners praising the encouragement at aid stations and the positive post-race vibe, complete with food and celebration for all finishers, including "highly coveted Slow A$$ awards" for those who finish dead last in each division. The out-and-back courses for the 50K and Marathon begin at the Dunns Farm Trailhead, promising a full immersion into this unique Florida wilderness.