I’m Will and I’m Hiking the Appalachian Trail

A photo of me at Bryce Canyon National Park.

Me at Bryce Canyon National Park in Utah ahead of a weekend backpacking trip with friends.

In fall 2023, I became obsessed with the Appalachian Trail. I was considering quitting my job as a writer at Forbes to attempt a thru-hike. It had always been a dream of mine, but never one I really took any steps to achieve. I dreamed about it for a long time, but always in the abstract. I wanted to change that. I wanted to actually go through with it.

Ever since I graduated university in 2021 and started a job as a newspaper reporter, I’ve felt like I jumped into my career too quickly. While I’ve loved being a journalist, particularly a local newspaper reporter, I regretted not doing something adventurous before starting my career. Life is too short to just work a 40-hour work week nonstop for the rest of my life. I needed to scratch this itch for adventure.

I’ve long loved the outdoors, camping and hiking. Growing up, my dad would take me camping and backpacking and I went camping a lot as a boy scout. One summer during college, I worked as a licensed canoe guide in the Superior National Forest of Minnesota at a youth scout camp. And I’ve continued camping with friends as an adult. I love the outdoors, so the Appalachian Trail felt like a great way to scratch that itch.

If you’ve been on this site much, you most likely know this, but for the uninitiated thru-hiking is where you hike the entirety of a long-distance trail within one year. The Appalachian Trail, which starts in Georgia and runs approximately 2,200 miles through the Appalachian Mountains until it reaches central Maine, is one of the most famous long-distance trails in the world. Thousands of people attempt to hike it every year and an estimated one in four succeed, according to the Appalachian Trail Conservancy.

Making it happen

When I visited family for Thanksgiving, I annoyed the hell out of everyone yapping about the trail and how I think I could thru-hike it. I was talking big game about quitting my job and doing it. While it was true that my job at Forbes probably wasn’t a good fit for me, in reality, I was agonizing over the decision more than I was letting on. I was scared at the prospect of quitting my job to do something like this. To sum it up, I was full of it.

A photo of me looking up at an interesting rock formation.

Me during a day hike with a buddy at Starved Rock State Park in Illinois.

However, soon enough, the decision was made for me. Forbes informed me they would not be extending my contract like I expected them to. (It’s a really rough time to be a journalist for those that don’t follow the industry, which has been absolutely rocked by layoffs, business closures, and a general existential crisis.) That settled it. I decided that night, I’d be attempting my thru-hike in the spring, and I’m not looking back.


So, I’ve spent the past few months researching the trail online and in books, waiting for the good spring weather and getting increasingly excited while also becoming an appropriate level of nervous.

I made several trips to REI and Target, debated between whether I wanted to purchase the Osprey Exos 58 or the ULA Circuit backpacks (While it was a tough decision, I went with the Circuit.) and bought a power bank setup with an excessive amount of charging capability to assure my caring, but terrified, mother that I would be able to stay in contact during the trip.

I read Chris Cage’s incredibly helpful book “How to Hike the Appalachian Trail,” Zach Davis’—who is also the founder of this site—essential mental and psychological guide “Appalachian Trials” and the famous—though, respectfully, in my opinion, a little overrated—“A Walk In The Woods” by Bill Bryson. All the while, I scoured TheTrek.co before deciding to apply to write for it.

A photo of me with my pack on

Me all geared up and ready for a practice hike.

I ran a marathon in December which I believe will help my fitness on the trail, and I’ve been walking all around Chicago where I live for practice, though people who live in or have visited the city likely know how it had a rather flat topography.

My built up excitement

Throughout all this, I’ve become incredibly excited. I’ve been obsessively watching YouTube videos (shoutout KyleHatesHiking and Homemade Wanderlust), reading some of my now-fellow bloggers’ posts and having to answer all the weird and quirky questions I’ve gotten from friends and family. You won’t believe how many people I had to tell I wasn’t bringing a gun. However, I was even more surprised by how many people were curious about the romantic scene on the trail. Some of my favorite remarks were “Tinder gonna go CRAZY out there” and “Its a drug filled orgy from what I’ve heard.”

Well, I guess I haven’t stepped foot on the trail yet, so I can’t say definitively, (though, I’m sure some romances happen) but I’m really not expecting—nor seeking out—any orgies. What I am expecting is a chance to spend some time in the beautiful outdoors, to meet some awesome people along the way and have the adventure of a lifetime.

A photo of five books: "How To Hike Appalachian Trail," "A Walk in the Woods," "Appalachian Trials," "The A.T. Guide" and "Appalachain Trail Thru-Hikers' Companion."

These are the books I’ve purchased ahead of my hike. I plan to bring “The A.T. Guide” with me and leave the “Appalachian Trail Thru-Hikers’ Companion” with my family so they can follow along.

I’m super excited to write about that adventure and the people I meet out there. I’m starting my thru-hike this week, and I hope you’ll read along. You can also follow me on TikTok, (I created a TikTok account just for this trip, so stay tuned to see how I use it.) Twitter and Strava (I’m going to see how feasible it is to track my hike using my Garmin sports watch, so follow along for that.) at @WillSkipworth.

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Comments 14

  • Секс Куклы : Mar 6th

    Awesome article. You are a very good author. It was a real pleasure to read.

    • Will Skipworth : Mar 7th

      Thank you! I appreciate the kind words.

      • Lorinda : Mar 9th

        Wanna know what its really like?
        Hiking Through: book by Paul Stutzman
        I READ IT IN 2018 before my through hike. It is right one!

      • Jody Williams : Mar 13th

        I live in Kentucky close to not on the trail though, but I’ve always thought about and wanted to . Now it seems I’ve got diabetes and had a toe nail removed yesterday and a few fell off so won’t be tomorrow except I’m not going to give up. But I’m 48 so gotten do some lifestyle changing. Be safe, be careful, have fun make memories and enjoy your life that’s the thing we all should do but you especially on that trail.

  • Henry Latimer : Mar 6th

    Live in Evanston, work in loop. Thru’d in 2021. Happy to meet for coffee.

    • Will Skipworth : Mar 7th

      That’d be awesome. What’s the best way to get in contact?

  • Linda Armentrout : Mar 7th

    Wishing you good luck for a safe thru hike. Looking forward to following your hike!

    • Will Skipworth : Mar 7th

      Thank you!

  • Sue Tyas : Mar 7th

    Greetings from Ontario, Canada
    It’s a dream of mine to hike the A.T also.
    I retire next year then after that I hope to get more serious but for now I’ll have to live vicariously through people like you and Dixie.
    I’m also looking for someone to hike the A.T. with.
    I’ll look forward to seeing your blogs when you post.
    Happy Travels,
    One step at a time,

    • Will Skipworth : Mar 8th

      Thank you! I’m super excited to hear you’ll be following along. If you put your email into the subscribe box, you’ll get an alert each time I post.

  • Patty nino : Mar 8th

    Best of luck, this is awesome

    • Will Skipworth : Mar 8th

      Thank you, I appreciate the kind words!

  • Flash : Mar 8th

    Good luck and thank you for sharing your experiences with your readers. I can’t wait to read more about your journey. BTW because I’m from Wisconsin I feel compelled to advise you to eat some cheese on the trail whenever it’s feasible. Just saying.

    • Will Skipworth : Mar 8th

      Thank you! I’m excited to hear you’ll follow along! If you put your email into the subscribe box, you’ll get an alert each time I post. Also, I love Wisconsin! Great state. I, for one, struggle not to romanticize the Midwest!


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