Those Hills Will Not Hike Themselves

343 miles, 11 Months, 1 Epic Adventure

That is the tagline that started my current backpacking journey. During the height of Covid, daycares in Kentucky were closed and I was pulling double duty working from home and taking care of my two daughters (aged 10 and 2 at the time). After just a week that dynamic was a bit much to handle, and after 4 months I was looking for a way to decompress. My wife and I had some vacation time scheduled, but nowhere to go. And the thought of a “staycation” at the house was not exactly exciting. So I decided to do something outdoors, to just get away for a bit and spend some time in nature. I immediately thought about backpacking and started looking for trails near me, which is when I came across the Hiker Challenge.

The Sheltowee Trace is a 343-mile National Recreation Trail in Kentucky that stretches through the entire length of the Daniel Boone National Forest in Eastern Kentucky, down to the southern boundary of the Big South Fork NRRA in Tennessee. It was named after Daniel Boone, who received the name Sheltowee (Big Turtle) from the Shawnee Indians when he was held captive by them. The Hiker Challenge is a program hosted by the Sheltowee Trace Association (STA) that gives hikers the chance to section hike the entire trail from end to end over one year. This unique opportunity breaks the Trace up into 11 sections, each one ranging from 25 – 35 miles, and hiked over the course of a. The STA takes care of all the logistics of camping and shuttling, and a hiker just has to show up ready and able to backpack that section’s miles throughout the weekend.

The Sheltowee Trace stretches from Morehead, KY to Northern Tennessee

Learning the ropes

When I first heard about this Challenge, I was immediately hooked on it. I am not in a position where I can take a month off of work to hike the entire trail, but I can easily hike one weekend a month! And so in July of 2020, I bought my first backpacking gear, intending to complete the Hiker Challenge in 2021. A friend and I were talking about this and he mentioned that he liked to backpack as well. We went on an overnight trip to the Red River Gorge, and I learned so much from just that one trip; everything from packs, to clothes, sleeping pads, and most importantly, where to look for information. I had no clue until then that there was an entire YouTube and podcast backpacking community out there. Discovering these resources was a game-changer for me. I immediately soaked up all the information I could and started researching different gear that I could replace. It will come as no surprise that I am only using one piece of gear from my original backpacking set purchase. Everything else has been replaced with better gear.

We went on two more trips that year; the Cranberry Wilderness in West Virginia, and the Roan Highlands section of the Appalachian Trail, backpacking from Carver’s Gap to Highway 19E. When these two locations are your first few backpacking trips, it is easy to get hooked. Cranberry Wilderness was magical and memorable, and the Roan Highlands were mystical. We slept at the Cloudland hotel site, waking up among the clouds and then conquering the Humps. I will always remember my first time climbing out of the valley where the old red barn (RIP!) was and then reaching the top of Big Hump Mountain.

The iconic red barn

The story so far…and what is to come

I spent 2021 going on lots of solo backpacking trips near me, getting more comfortable with backpacking, camp setup and tear down, and navigating trails. I had a memorable trip to Dolly Sods in West Virginia, revisited the Roan Highlands, and hiked with a group in Northern Tennessee. In 2022, I did complete the Hiker Challenge and it was everything that I was expecting!

This year I am going to participate in the Hiker Challenge again, with the first hike starting in the middle of January. I want to let more people know more about this unique experience and hopefully encourage some other Trail Associations with trails of similar lengths to start a similar program. I am looking forward to revisiting the Challenge this year and reuniting with old friends along the way. You can expect monthly updates from me as I prepare and finish each section.

I also plan on attempting a thru-hike of the Foothills Trail in South Carolina. At 77 miles, this is a perfect week-long adventure that I can knock out and I will be sharing my experiences on that trail as well. I have a nephew who is graduating High School next year, and he has recently told me about his plan to backpack in Africa and Europe afterward. He has invited me along, and if the timing lines up, I hope to be able to report back on these adventures.

I hope you enjoy reading about these journeys on which I am about to embark!

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Comments 4

  • Ruth Morley : Jan 1st

    Richard, I was excited to find your post about the Sheltowee challenge because it has been on my radar screen for several years now. Living in Cincinnati, I’ve hiked several times in Red River Gorge, where I’ve seen the turtle emblem as a blaze on the trees in some sections. For now, I’ve been busy with the Colorado and Florida Trails, and have Ohio’s Buckeye Trail as an ongoing hiking project in short sections.

    I’d be pleased if you’d check out my blog, also here on Also, on Zach Davis’ YouTube podcast Backpacker radio you’ll find me in one of his November podcasts.

    Happy hiking! I look forward to following your journeys.

    • Richard Murray : Jan 2nd

      Thank you! I did catch that episode of the podcast and was excited when you mentioned the Trace.

      Surprisingly, there are a lot of people from the Cincinnati area who participate in the Hiker Challenge.

  • Patrick : Jan 2nd

    I just learned about that program yesterday and was bummed I’m late to the game. Hopefully next year though!

    • Richard Murray : Jan 2nd

      There is still time! The Director is really flexible and I am sure they would take more peeople.


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