Section 1 begins at the northern terminus trailhead off KY‑377 just north of Morehead, at the northern boundary of Daniel Boone National Forest in Rowan County. The trail then runs south roughly 25 miles to Morehead, where the Sheltowee Trace follows roads and sidewalks right through town, to the endpoint. The end of Section 1 feels special for starting our southbound journey, the challenge switches direction every year.

Morehead State University is my alma mater, so walking through campus again will be a bit of a homecoming. It’s been many years since I last did that, and I’m delighted to walk on the heated sidewalks—a fun little MSU perk that still makes me smile.

Pre-Hike Prep

Over the last eight weeks, I’ve gone from “throw a snack in a daypack” hiker to “please don’t let this weigh more than a small child” weekend backpacker. I’ve bought all the gear I think I need to hike 25–40 miles each weekend I’m on trail, and I’m sure the trail will be happy to prove me wrong. I’ll do a full rundown of my setup after Section 1 so I can talk honestly about what worked, what flopped, and what I swore I’d never carry again but somehow will. One of the best perks in these first three months is the 5 lb “drop bucket” for our heavy winter gear. That’s an absolute lifesaver—for us newbies and, honestly, for anyone who doesn’t want to haul winter “worry”.

To get ready, I went to an orientation at Quest Outdoors hosted by the Sheltowee Trace Association. They walked us through what to expect, how to prepare, and officially welcomed us into the long line of hikers who have attempted this challenge. Hearing the numbers hit different: 253 people signed up last year, 151 actually showed up for the first hike, and only 50 finished the full Sheltowee Trace end to end. No pressure, right?

My nerves this past week have been ping‑ponging between total breakdown, chaotic excitement, and something in between. I’ve packed my pack, unpacked it, and repacked it four times. The recommendation is to pack on Thursday night and then leave it alone so you can relax and not forget anything on Friday. Naturally, I did exactly the opposite and tore into my sleep system again today “just to be sure.”

The good news: laying everything out and seeing my setup actually felt good. I did make a last‑minute change and went back to my hammock, but this time I’ll be using it on the ground with a ground sheet, like a one‑person tent. It’s designed for that, and with lows around 16 degrees going into Sunday morning, I decided I’d rather lose less heat in a smaller space than spread out and freeze in a two‑person tent. I still have the option to hang if I want. I’ve got a quilt and sleeping bag combo that should work like a top and bottom quilt system, whether I’m on the ground or in the trees.

My biggest fears heading into this weekend: the COLD and back‑to‑back 12‑plus‑mile days. I’ve never done that distance on consecutive days, and I’m about to find out exactly how I feel about it—ready or not.
The alarm is set for 4 a.m. so I can make the drive to the shuttle pickup by 6:30 a.m. Pack is finally packed and weighs at 21.3 lbs before my water is added. Nerves are high. Excitement is higher.
Let the adventure begin.