The Harpeth Hills Flying Monkey Marathon in Brentwood, Tennessee, is not your standard race—it’s a relentless test of endurance through a forest that refuses to be tamed. Covering 26.2 miles with over 3,500 feet of elevation gain, this marathon tackles steep climbs, rugged terrain, and dense woodland trails that demand both stamina and respect.

From the moment you set off, the forest comes alive. Tall oaks and maples crowd the path, their branches swaying as if daring you to press onward. The Harpeth River occasionally whispers from below, its currents pushing against the banks, reminding you that this landscape favors the persistent. The course weaves through rolling hills that force you to engage every muscle, trading long stretches of running for strategic hiking sections.

Expect rocky footing, exposed roots, and occasional muddy patches. Each mile is an invitation to balance focus with forward momentum. When the terrain lets up, you’ll catch glimpses of sweeping views over the valley—brief, earned rewards that make the struggle worthwhile. The air here carries the slow hum of wildlife, and if you’re quiet, a deer or two may watch with unblinking eyes.

Preparation is key. Good trail shoes with reliable grip are essential to tackle slippery descents and uneven ground. Hydration packs or handheld water bottles will keep you fueled; water stations are spaced but not abundant. Start early to avoid the midday heat, particularly in late summer, when the Tennessee forest grows thick and humid. Spring and fall offer cooler temperatures but be ready for sudden weather shifts.

Navigating the Flying Monkey isn’t just about crossing the finish line; it’s about engaging with a landscape fiercely itself, one that challenges every runner and walker to find their rhythm against its pulse. This course tests your physical limits while grounding you in the raw, uncompromising beauty of Tennessee’s Harpeth Hills.

Whether you’re chasing a marathon PR or simply out to conquer a unique trail experience, this race rewards grit, preparation, and respect for a trail that makes no apologies. Plan well, pace yourself, and let the forest’s own energy carry you through an adventure that’s as demanding as it is unforgettable.