Breaking Trail: Making Lemonade Out of My Midlife Crisis

Dreaming Big

If you’re reading this, you likely remember the first time thru-hiking a big trail became a dream. For me, I was a tween Boy Scout in the mid-90s. A former Scout from our troop regaled us of the epic 2,000 mile hike he just completed in Maine. The scenery, the wildlife encounters, the physical rigors, the emotional challenges. I may have been young, but I knew I. Wanted. That.

Soon thereafter I picked up Bill Bryson’s “A Walk In the Woods”, as many aspiring thru-hikers surely do. I left the read more emboldened to set off on an Appalachian Trail adventure, writing off the author’s conflict with his attempted thru-hike as an issue of age. Surely I won’t be as turned off by the experience, I reasoned. I’ll finish the A.T. long before I’m that old (Bryson was 44 during his attempted thru-hike).

Life Gets In The Way

To save you the suspense, I’m now nearly that old, without an A.T. thru-hike to speak of. ‘Gap years’ were practically unheard of when I went to college, and the right job opportunities at the right (wrong?) time kept me from taking a six-month leave.

Summiting my 46th Adirondack High Peak in 2017

Summiting my 46th Adirondack High Peak in 2017 (I hiked with a bit more traditional attire, I swear)

Sure, I still found time for hiking and backpacking through my 20s and 30s, mostly as bite-sized weekend forays in the High Peaks of New York’s Adirondack Mountains or short sections from the Smokys to the Whites. I even tested the waters (well, mud) of a true thru-hike by completing the Long Trail in Vermont in 2016, joining the A.T. bubble for the first 100 miles. While that experience left me convinced more than ever that I wanted to tackle the big one, a mere two weeks after returning from the Canadian border, I met my wife and life accelerated.

Northern Terminus of the Long Trail at the Canadian border in 2016

Celebrating the end of my Long Trail thru hike (a.k.a. End-to-Ender) in August 2016

Turning My Midlife Crisis Into An Opportunity

In the blink of an eye, I was approaching my 39th birthday. With a mortgage, a stable job, and above all else a loving family, the idea of escaping to the trail for several straight months felt unrealistic and irresponsible. But I couldn’t escape that feeling of remorse for letting prime opportunities to traverse from Springer to Katahdin in one shot pass me by. I also feared waiting until retirement was risky, with so much uncertainty about my health decades down the road. And while I yearned for the challenge of what I long considered a true thru hike, the thought of giving up on my dream altogether? Oh, I simply couldn’t. I felt I needed to do something, and fast.

My loving family

This is my loving family. Who would even think of leaving them for six straight months? Not this guy!

So in September 2023, with the blessings of my wife and kids, I flew down to Atlanta to begin hiking NOBO, one section at a time.

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Comments 4

  • alexis mcallister : Jan 20th

    Go for it. Some of my best memories on the trail are the adventures my sons and I had on the trail. Been a thru, then now section with my sons. Love section because every year it gave us the continued adventure. No end. Always next trip to look forward to. They have less then 500 miles left. See you out there. Mery Poppins

    Reply
  • Fun Size : Jan 20th

    KAZANOBO, I can’t wait to see you on the trail!! I start my flip flop thru-hike in Virginia in March. I hope we will run into each other.

    Reply
  • Doublepack : Jan 21st

    Looking forward to following your journey to Katahdin. I began section hiking with my son in 2012 and have travelled from Springer to Williamstown MA as of last summer. Starting at age 50 I have learned so much with each section I have completed. Each one has been new and exciting Hope to see you on trail and best of luck!

    Reply
  • Jess : Jan 27th

    Tomorrow isn’t promised! Appreciate your reflections on that, and turning those realizations into actions. Thanks for sharing your journey Tom!

    Reply

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