
Five years into my commitment to backpack the entire Appalachian Trail, I had completed almost half of the Trail.
But there was still another half waiting for me.
By this point in my journey, I had lost count of how many Plan Bs I’d encountered. Hiking plans changed, unexpected obstacles appeared, and things didn’t always turn out the way I had hoped. But each time, I surrendered my will to God’s and kept on going.
Until one particular day in New Hampshire’s White Mountains.
That was the day I was ready to quit.
For good.
The Day I Almost Gave Up
I had gotten caught on top of Mt. Madison in 65-mile-per-hour winds, fog, and even sleet. It was a frightening experience, and by the time I reached the safety of Madison Springs Hut, I’d had enough.
No more Plan Bs.
I was done.
I was so disappointed with the way that entire trip was going that I convinced myself I didn’t care if I ever stepped foot on the Appalachian Trail ever again.
My motivation, commitment, and desire to see this eleven-year goal through had disappeared.
I told myself I was getting too old for these kinds of shenanigans. After all, no one else really cared whether I finished this blasted Trail or not.
So why should I?
I had already hiked more than 1,000 miles. I had experienced some incredible adventures, witnessed extraordinary beauty, and learned a great deal along the way.
Maybe that was enough.
At least, that’s what I was telling myself.
A Conversation That Changed My Perspective
Back at the Highland Center Lodge, safely off the mountain and even enjoying some sunshine, I met two women who worked for L.L. Bean, the outdoor outfitter headquartered in Maine.
We shared a bunk room, and I told them about my harrowing experience on Mt. Madison the day before.
After listening to my story, one of the women offered a simple piece of advice:
“You just need to find hiking partners with the same priorities as you.”
Wow.
Five years of backpacking. More than 1,000 miles on the Appalachian Trail. Nine different hiking partners.
And that concept had never crossed my mind!
I had been so focused on finding people willing to hike with me that I hadn’t given enough thought to finding people who approached hiking with the same priorities I did.
Suddenly, I began to see my situation differently.
Maybe I wasn’t too old. Maybe I wasn’t incapable of finishing. Maybe I simply needed to find the right people to share the journey.
And just that quickly, my resolve to finish the Trail was restored.
But there was still a rather significant problem.
Where was I going to find these hiking partners?
Finding someone near home who wanted to join me for a day hike was difficult enough. Finding women willing to travel hundreds of miles and backpack for days through some of the most challenging terrain on the Appalachian Trail was another matter entirely!
But God…
An Unexpected Connection

What I hadn’t fully appreciated at the time was that God had already begun putting the pieces together.
Earlier, when I finally reached the safety of Madison Springs Hut, I encountered a group of women hikers.
Among them was a woman named Lynn, who lived in Tennessee, just a few hours from my home.
We exchanged contact information before I left for more comfortable lodging for the remainder of my trip.
At the time, I had no idea how important that seemingly ordinary connection would become.
The following year, Lynn reached out and invited me to join her and several other women for another hike through the White Mountains.
I was thrilled!
But I was also nervous.
The advice from the woman at L.L. Bean was still nudging at the back of my mind.
Would Lynn and the other ladies have the same hiking priorities as I did?
What if they were elite athletes disguised in middle-aged women’s bodies?
Would they be willing to hike at my pace, or would they leave me behind? Could I even keep up?
After my experience on Mt. Madison, my hiking confidence wasn’t exactly at an all-time high.
And, of course, I wasn’t getting any younger!
But God…
The Blessings I Never Saw Coming
As it turned out, Lynn, Mary, and Alina became my hiking partners for the remainder of my Appalachian Trail journey.
Together, we tackled some of the most difficult miles I had yet to hike.
Other women joined us along the way, including Jessica, who, along with Mary, would eventually stand beside me on the summit of Mt. Katahdin.
But these women became much more than compatible hiking partners.
They became friends.
Our friendships extended beyond the Appalachian Trail and onto other trails and into other parts of our lives.
And to think, these relationships began taking shape during one of the most discouraging experiences of my entire journey!
Had everything gone according to my original plans, I wonder whether our paths would ever have crossed.
When My “Plan B” Is Actually God’s “Plan A”
I continue to be amazed at how God takes what I consider subpar Plan Bs and turns them into His glorious Plan As.
What I saw as a miserable, frightening experience on Mt. Madison became part of a much bigger story—one that included new friendships, renewed confidence, and the opportunity to continue pursuing a dream I had nearly abandoned.
One of my favorite reminders comes from Romans 8:28:
“And we know that God works all things together for the good of those who love Him, who are called according to His purpose.”
That doesn’t mean every difficult experience suddenly becomes pleasant or that every disappointment turns out the way I want it to.
But it reminds me that God can be at work in circumstances I would never have chosen for myself.
Looking back, I can see how He was putting people and opportunities in place long before I understood what I needed.
Sometimes I wonder how many other blessings I’ve nearly missed because I was so focused on what wasn’t going according to my plan.
I’m so thankful God doesn’t limit His plans to what I can see or imagine.
And I’m especially thankful that He can take what I consider a disappointing Plan B and turn it into a blessing I never saw coming.
Want to read more about the unexpected turns, challenges, and blessings along my eleven-year Appalachian Trail journey? Explore my Facing Fear Through Faith memoir trilogy.
You can also experience the journey through my Appalachian Trail Photo Journals at JackieMcKool.com.