Hiking Stories: Learning on the Direttissima

Greg Benedis-Grab
8 min readSep 16, 2021

Why would someone undertake a solo hike climbing 48 mountains in one continuous trip, covering 235 miles of the most rugged landscape that New Hampshire has to offer?

Could it be that I wanted to find solace in the wake of the death of my father, the one who first introduced me to the outdoors? Maybe it was needing to find calm after supporting technology at a PreK-12 school during a global pandemic. Or was it a nature-forward mid-life crisis? Luckily I had a lot of time to ponder the why during the nine days it took to complete.

The White Mountains is a beautiful forest in central New Hampshire. The Appalachian Mountain Club identified 48 of the mountains of this forest in excess of 4000 feet and created a ‘club’ for people who endeavor to climb all of them. The challenge has become infectious and many of the hikers that you encounter on the trails will note how many from the list they have completed. When I was looking for a summer challenge in the White Mountains, I came across what is called the Derittissima. The term refers to any route that summits all 48 peaks in one trip. This is not a small undertaking as it requires at least 235 miles to climb all of them. Also many of the trails are quite challenging. Yet this seemed like the right challenge for me, because I love hiking, sleeping outdoors, and pushing myself physically. Also I have a zeal for going uphill. In my childhood I learned how to walk and even run comfortably over rocky terrain full of roots, and somehow I have maintained that skill into middle age. Finally, I love route planning, particularly when it has a mathematical component to it. You could probably use a computer to optimize this route which could be a fun future blog post. For this trip I created a route on Gaia GPS (a topographic map mobile app) which calculates the total distance for you. The planning also involved carefully selecting gear, getting into shape, considering safety factors, and figuring out transportation to the route start. Then there are all the challenges that spontaneously arise during the trip.

On my last evening of the journey I was making the steady climb up Mount Waumbek, the forty-seventh peak on my route. With over 200 miles under my belt, my body had become a hiking machine, practically floating up the trail. My metabolism was burning through 6000 calories a day and it was difficult to pull out sufficient snacks to sate my growing hunger. Unfortunately, during this balmy evening there was barely a breeze even as I climbed higher and higher up the slope. I could feel the sweat starting to accumulate on my brow, shirt and legs. Then the clouds rolled in and the sky darkened. It was a relief when I felt the first drops strike my shirt. As the rain started to wet my body and lower my core temperature I pulled out rain gear. Ten minutes later the rain was coming down hard and I threw my poncho tarp over my pack and body. I kept moving through the relentless rain as a river formed on the trail. There was something satisfying about knowing that I had everything I needed to thrive in the situation. In fact my gear was designed to thrive in any situation the White mountains could throw at me. Maybe part of the purpose of this trip was proving that I could overcome all the problems that would undoubtably arise. Doing a long, complex route like the Derittissima guarantees a range of situations to overcome.

When I reached a clearing close to the top of the mountain I looked for a place to set up camp. It was about 20 minutes before sunset but it was already fairly dark and I pulled my headlamp out of the top pocket of my pack to improve visibility. At the same time I grabbed a ziplock bag full of cord and stakes that I would need for my shelter and placed them in my rain pants pocket. The clearing was a perfect site to pitch my shelter, open, flat and surrounded by trees. This would allow me to tie out my tarp to keep out the rain. I placed my backpack on the ground, removed my poncho tarp from my body and put it over the pack. I laid it out to prepare for my shelter configuration. My raincoat and rain pants were still keeping me dry as I worked methodically. From my pocket I took out the ziplock bag full of six foot cords and titanium stakes and attached a segment of cord to each tie out loop on the tarp. Some of them I connected to trees and others I ran to the ground where I placed a stake. After attaching the final cord I had created an A-frame structure that protected my gear from the rain and the wind. I then tightened each cord carefully. The heavy rain ran down the tarps semi-translucent SILnylon material to the ground. I then ducked under the tarp, removed my rain gear and set up my ground sheet, bivvy, sleeping pad, and quilt. At this point I could feel my core temperature starting to drop from having stopped hiking. I quickly slipped into my sleeping bag and immediately felt warmer. I went through my evening routine including preparing and eating dinner, organizing my gear, considering what I would need in the morning, and brushing my teeth, all under the dry comfort of the tarp. As I lay down to fall asleep, I marveled at the fact that the relentless rain instead of being a nuisance was a challenge that made the evening more interesting and even enjoyable.

An important take away from the Direttissima is that an experience is often what you make of it. I could have been hating life as the rain pounded on me. Instead I embraced it. There have been times when rain has gotten me down and even made a trip seem like a mistake. On this day the rain became a lasting memory of the trip reminding me of my level of preparation. Maybe this is a case for optimism. Being optimistic and taking a positive outlook made this evening a lot happier.

As I reflected on the rain event I considered the careful planning that had gone into the gear in my bag. In the weeks leading up to the trip I evaluated each item in my pack and pared my gear down to the minimum possible to keep me safe and comfortable. My decisions were also based on all my previous experiences hiking and using gear. I was proud that I had reduced my base weight to ten pounds not including food and water. Traveling light makes covering large distances much more enjoyable.

Another way to look at the challenge of a rainstorm is that it is a learning experience. It took me years to develop my camp routine, to develop my ability to pitch the tarp in heavy rain. To have the confidence to set up camp in the rain and be assured through every step. It took time and learning to get to the point where I could enjoy that rainstorm. I could say the same thing about many aspects of my outdoor travel including route finding, hiking endurance, and managing nourishment. Hiking the Direttissima provided me many opportunities to put all this learning to the test and to do some more learning along the way.

When I first considered planning a summer trip I thought about it as a form of meditation and a way to challenge myself physically. I think those aspects of the experience were true. But this trip was equally about creating the optimal environment for learning. In fact I am starting to think that the reason I love the outdoors and backpacking is that it is so infused with learning. Throughout the entire trip I was learning new skills, honing my abilities and drawing on previous learning to persevere. There is no end to the learning that takes place when you challenge yourself in nature. And when you overcome the challenges the sense of accomplishment is powerful.

On the second day of the trip I had planned to leave the trail for two miles in order to save a number of miles of travel. The plan was to drop down the east slope between Mount Lafayette and Mount Lincoln. The slope is a known rock slide that is described in detail in various blogs. The good news is that I had the advantage of my GPS enabled phone where I could look at topographic maps and satellite imagery. The bad news is that it was raining and those rocks were slippery. I was able to descend the steep slope safely, but I had to test each step before trusting my weight on it. I used all I have learned hiking through the White mountains over the years. When I got lower down on the slope I found a river that I could walk through which helped me avoid the dense trees on either side. By the time I got back on the trail my brain was exhausted from so much concentration on traction, foot placement and route finding. Going off trail requires an entirely different mindset about the outdoors and I like to find ways to spend some of my time off set trails when it is possible.

On the fourth day of my journey I left camp before sunrise. When backpacking, I like to pack up quickly in the morning and get moving for a while before eating breakfast. On this morning I reached the top of Mount Bond to eat and watch the sunrise. As I looked out over the ridge I thought to myself, I might be in the most beautiful place on Earth. The mist clung to the distant ridges as the sunlight illuminated bright orange clouds all around me. I took out my phone and took a picture of the landscape. When I looked at the image I realized I had not adequately captured the beauty. The scene was certainly stunning, and the Bonds are possibly the most picturesque part of the White mountains, but the feeling I was experiencing was not about visual perception. It was much more than that. It was the cool morning air. It was my body working to summit a peak before 6am. It was the carefully assembled gear in my backpack. It was the ensemble of planning that goes into making a trip work from moment to moment. It was the world of learning that was unfolding for me on the Direttissima.

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Greg Benedis-Grab

exploring the intersection of coding, education and disciplinary knowledge