For years, Cliff Mountain lived rent-free in my head.
Unlike many of the Adirondack High Peaks, Cliff seemed to exist mostly in stories. People talked about it. People climbed it. People casually mentioned doing Cliff and Redfield together, which always left me wondering if they possessed some sort of secret superpower or simply had much larger demons than I do.
Meanwhile, I was over here building Cliff into that one intimidating relative at family gatherings.* The one you spend years hearing stories about, avoiding eye contact when possible, and hoping someone else deals with them first. Eventually, though, you know you’re going to have to introduce yourself.
Part of that was because I could never find many photos of it. You can look up Algonquin, Marcy, Giant, or Cascade and find thousands of pictures. Cliff somehow manages to hold onto a little mystery. So, naturally, my brain filled in the blanks and created a mountain that was probably twice as terrifying as the actual one.
It didn’t help that I spent years thinking Cliff Mountain was named after a person.**
A person.
Named Cliff.
It seemed rational enough. Plenty of Adirondack mountains are named after people, right?
Nope.
When fellow hiker Jim Pedley informed me that the mountain was, in fact, named after the actual cliffs on the south side of the mountain, I felt two things simultaneously.
First: embarrassment.
Second: immediate concern.
Wait.
It’s named after the cliffs?
That seemed significantly worse.
By the time this spring rolled around, Cliff had become one of the peaks looming largest in my remaining High Peaks journey. Not because it was the tallest. Not because it was the longest. Simply because it was one of the mountains I had spent years imagining.
The original plan was Cliff and Marshall.
Looking back, that feels adorable.
Haha. Funny me.
As my hiking partners Rochelle, Court, and I made our way past Lake Colden and toward Uphill Lean-to, reality slowly began tapping us on the shoulder. Also, I would like to officially state that those were some of the longest true “Adirondack miles” I have ever experienced. I am 100 percent convinced someone was out there extending the trail right in front of us. And though I didn’t cry that time, in the past, I absolutely would have.
The miles were adding up. And Cliff was still waiting.
Somewhere along the trail we collectively came to the conclusion that “just Cliff” was more than enough adventure for one day. I laugh at that phrase now because there is absolutely nothing “just” about Cliff Mountain.
One thing I’ve learned through hiking is that social media is a terrible way to judge what mountains actually feel like. Online, you see summit photos. You see people smiling. You see accomplishment.
What you don’t always see are the moments where people are working through doubt. Sometimes quietly. Sometimes through a fit of Tourette’s-level colorful language. You don’t see the fatigue, the uncertainty, the occasional tears, or the realization that maybe you should have packed one more sad burrito.***
Those moments are where the real story lives.
As we climbed higher, I found myself thinking less about the summit and more about the people around me.
Rochelle and Court are both strong hikers. What impresses me most is their willingness to not tell me “no”.
They have witnessed their fair share of Toddler Jess on trail. They have received random text messages proposing objectively ridiculous adventures. Yet somehow they continue agreeing to them.
I honestly don’t know what’s wrong with them.
But I am grateful for it.
There are moments on mountains like Cliff where confidence isn’t loud. It doesn’t look heroic. It looks like someone stopping, looking at a steep section, taking a breath, and continuing anyway. It looks like trusting your feet. Trusting your body. Trusting your preparation. And occasionally muttering something unprintable before proceeding upward.
That day, I watched both Rochelle and Court do just that.
At one point, I found myself almost stepping outside the moment and simply observing the three of us moving through the cliff sections. Watching my friends climb was every bit as fascinating as the terrain itself. There were multiple points where hands became just as important as feet, and while nothing felt impossible, it absolutely demanded attention.
This was not the kind of hike where you could put your head down and just cruise. You had to be present. You had to engage with the mountain. You had to earn it.
That is one of the beautiful things about having hiking partners. You get to watch people push themselves, problem-solve in real time, and move through hard things right in front of you. And they did exactly that.
What surprised me most was how quickly the fear I’d carried for years started to fade. It was not because Cliff became easy. It didn’t. Not because it became less steep. It wasn’t.
The fear faded because uncertainty was replaced with experience.
The intimidating relative I’d built in my imagination finally had to compete with reality, and reality turned out to be far more likable than the story I’d been telling myself.
The long walk out was exactly what you’d expect. Tired legs. Shared misery. Random conversations that only make sense after ten-plus miles in the woods. Equal parts laughter and suffering. Random songs we have made up over 100’s of miles of trail together. (We are still waiting for our record deal….)
My favorite kind of Adirondack day.
As we made our way back toward the trailhead, I found myself thinking about all the hikers I admire. The ones who tackle Cliff and Redfield together. The ones who stack multiple peaks into a single day. The ones whose adventures continually push me to reconsider what I believe I’m capable of.
For years, I assumed those people possessed something special that I lacked.
Now I wonder if that’s not true at all. Maybe they simply started. Maybe they took one step. Then another….Then another….Maybe confidence isn’t what gets us up mountains. Maybe confidence is what we collect along the way.
Cliff Mountain earned every bit of its reputation. It was long. It was challenging. It demanded effort. But in the end, the biggest obstacle wasn’t the cliffs. It was the story I had been telling myself about them. And like so many things in life, the only way through was to stop imagining and start climbing.
Footnotes:
* Not MY family gatherings…. I’ve just heard of others having these situations….
** I am not proud of this. But I believe in transparency.
*** A sad burrito is a burrito you packed while you were happy, BEFORE the hike. Then, while grumpy in the forest, these usually turn into sad burritos. They don’t quite make you happy again, but they make you less miserable.
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