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Why (and How) We Backpack: Two Backpacking Enthusiasts Share Stories of their First Trip

The backcountry can be isolated, remote and physically grueling. So why go there in the first place? And how does it actually feel the first time you do it?

At Headlamp, we are inspired by the journey of the outdoors in every sense. Where it starts, where it goes, how we change. For this week’s post, we highlight two stories of backcountry exploration from two women on their first backpacking experiences.

Do you remember your first adventure? What inspired you? Maybe it was an instinct, a need, a nudge from a friend. Whatever it was, we’d love to hear about it! Comment below or email us here.

“From the Ocean to the Trail: My First Backpacking Trip”

By Jennifer Villamin

I'm not exactly too sure why I started backpacking. I just know it was a long-awaited natural progression from my years of car camping and randomly hiking. I was already pretty athletic since I had already spent about 10 years racing competitive outrigger canoes with a local outrigger club in San Francisco, so my endurance was already there. But, I've never had the experience of carrying all of my gear for miles and miles before getting to a campsite. I was only 5 ft tall and never weighed more than 115 pounds. So, I never thought I would ever be able to carry that much weight of everything I would need to survive a trip. But, there was just something about it that just suddenly peaked my interest - for some reason.

Little did I know that my very first backpacking trip would be right at the start of the pandemic world shutdown, in 2020.

Before my trip, I reached out to some of my former outrigger teammates from the women's crew that I had stayed in contact with even after they stopped racing. I invited them, or rather asked them, to go on a little backpacking trip with me because I'd never been and wanted to experience it, but I didn't want to go alone. Two of my friends who said yes, luckily, already had at least one major backpacking trip under their belt, so my little beginner friendly trip I organized would had been pretty easy for them. They both were over 5' 8".

We went to Los Padres National Forest and found parking pretty close to the trailhead. Seriously, I cannot begin to tell you how excited I was when we finally found parking and we strapped on our gear. This is it! We made our way to the trailhead sign and took our obligatory photos in front of it. I was giddy. And anxious. But, very, very excited.

And then we started our hike, and it was practically straight uphill. This is it. I was finally doing it, I was hiking, and I was carrying all my necessary gear. I was finally "backpacking"! I can do this! I can totally do this! All 5 feet of me! And almost immediately, I was rewarded with some of the most amazing views of the Pacific Ocean and the California coastline that I had ever seen. And we weren't even at the top, yet! My senses were overloaded. The trees, the mountains, the views, the ocean, the coastline, the sights, the smells, the sounds, the birds soaring above, the gentle wispy breezes across my face, and the meditation of my footsteps through the miles of trail as I sipped on my hydration tube. I learned how to poop in the woods. It was a whole new world, and it was glorious!

On our last night on the trail, a torrential rainstorm blasted its way through the mountain. All three of us slept right through it, none of us heard a thing - we were wiped. Early the next morning, I suddenly woke up to a very cold floor. Still half asleep, I started thinking "Why is my sleeping bag suddenly so cold on the bottom?" I thought maybe I slid off my air pad? I finally sat up in my sleeping bag and tried to adjust it, and that's when I realized my bag was wet. Wet?? I felt around to everything else in my tent and realized the rain had soaked right through my tent. Everything. was. soaked. right. through. Everything. Even the clothes I laid out on top of my backpack to air out for the day. There was a thin layer of water on my tent floor. I didn't even know it rained. I had brought an old tent I used for car camping, it was the only tent I had, and had never been in a rainy situation with it before. So, it never even occurred to me to waterproof my tent before taking it out.

Newbie. Rookie mistake. Yep, I was a total beginner. Total lesson learned. The whole situation was so infuriating, I actually started laughing because I was so absolutely incredulous. Did this seriously just happen?? I started to plan for my next trip and what gear I would upgrade. The tent was number one on that list.

We packed up our things one last time and spent the rest of the day hiking back down to the car. Luckily, I was wearing merino wool and so I was not too cold hiking in my totally-soaked-through clothing and windbreaker. I was actually really quite warm. A lot can be said for merino wool!

As we drove out of Los Padres and headed back to civilization, we stopped at the nearest town for some snacks and a bathroom break. We found a Starbucks, but were confused by their handwritten sign on the door that said we were required to wear "masks" upon entering. None of us had masks, but all we had were our buffs, so we just wore those. We walked in and noticed all the tables and chairs had been pushed up against the wall and dine-in was not allowed.

It turned out, our trip happened the same exact weekend the world was starting to declare "shelter in place" orders due to a pandemic. A pandemic?? Shelter in place?? My friends and I were on top of a mountain in Los Padres National Forest in California while these orders were declared. Not only did I just come back from such an amazing experience, but I just realized I was now in the middle of an unprecedented global event that no one understood or could explain. That entire trip completely crystallized backpacking and the start of the pandemic for me. My life was changed forever.

It's only been two years since that very first trip, but I have, so far, managed to take two new local trips each year since then. I am totally in it now, backpacking is now a part of how I live my life, regardless of the distance. I still haven't really figured out why I started backpacking all of a sudden, but I definitely know why I will keep doing it.

Jennifer has spent the last 20 years participating in different endurance sports, notably outrigger canoe, and most recently just discovered backpacking during the start of the pandemic. She is currently in the very early stages of scratching her outdoor entrepreneurial itch by working on creating a line of ultralight backpacks for women, Two Girls Trekking, to be launched TBD 2023.

“I Need to Prove to Myself that I Can Do This”: Why and I How I Decided to Backpack

By Jini Chatterjee

I remember when I realized I wanted to go backpacking. I was on a day hike in Yosemite and saw a crew of dusty, fit-looking folks traversing on a trail ahead of me. Their faces were obstructed by the giant packs on their back but I could hear them laughing and singing. They looked strong and badass.

“I want to do that one day,” I told my partner. He seemed skeptical. We had just started hiking and trail-running with some regularity. Neither of us had grown up “outdoorsy”. “I think we would need someone to show us how,” my partner told me. “OK, sure!” I said. I was confident we could find someone. Backpacking looked fun. How hard could it possibly be to find someone who would take us on an epic adventure?

Pretty hard, apparently. I didn’t have many outdoorsy friends at the time, and nobody I spoke to was interested in carrying a heavy pack in the heat for miles without cell coverage or the idea of pooping outdoors. I was new to the outdoors so I wasn’t even aware that guided backpacking trips existed. After a few months of searching for and failing to find someone who would take me backpacking, it felt like backpacking was not “for me.”

Still, the thought of being immersed in wilderness for days was just too enticing. I couldn’t let it go. Honestly, it started to feel existential. At the time, I was struggling professionally. I had a fancy, secure job, but I didn’t feel satisfied at work and I was questioning my future. I couldn’t remember the last time I had embarked on something truly challenging.

So I became obsessed with the idea of backpacking. Yes, I was drawn to the views and physical challenge but more than anything, I wanted to prove to myself that I could do something I had never done before.

I begged my partner to give backpacking a shot with just the two of us. He was still skeptical, but agreed to come along if I planned everything. I picked a moderate out-and-back route in the Ventana Wilderness that was a couple of hours away from our apartment in San Francisco. I chose a straightforward route where most of the elevation accumulated early in the trail so that we would get done with the “hard stuff” early in the day. A few days before the trip, we bought gear from REI and borrowed what we didn’t buy from friends. The price tag was hefty, but REI assured us we could return our items after the trip if we didn’t like them (assuming they weren’t totally destroyed). I watched YouTube videos on how to pack and fit my backpack and how to use a bear canister (which turned out to be way more complicated than I thought it would be!) I remember feeling intimidated by the thought of carrying 20+ pounds of “stuff” for 16 miles but my backpack had excellent back and hip support and I was able to carry my gear around my apartment without feeling too uncomfortable.

Before we left on our trip, my partner and I agreed we would let each other know if we weren’t having fun. I remember feeling excited, scared and full of questions. What if we forgot something essential? What if I got injured or tired and couldn’t finish? What if I didn’t have fun? On the car ride to the trail, the questions kept coming and I could feel my nerves rise the closer we approached.

And then suddenly, we were at the trailhead and…started backpacking. The weather was beautiful: sunny, cool, not one cloud in the sky. As we trudged up the mountain, I could feel my anxiety slip away. The views on the trail were surreal: clear sweeping panoramas of the Pacific Ocean against mountains coated in wildflowers. The elevation on the trail was tough physically but we took plenty of breaks and moved at a moderate pace. We started early, so we had plenty of time to get to where we wanted to camp. When we reached the backpacking campsite, I was relieved to be able to rest my muscles. We unpacked our gear, pitched our tents, inflated our sleeping pads and found a small creek for water. The whole operation felt much smoother than I expected. I was glad we had spent time preparing for the trip. Even though our gear was new to us, we had made sure that we were familiar with it and had walked through our plan before leaving. When the night finally descended upon us, I remember crawling into my tent feeling happy and proud, like there was nowhere else I'd rather be.

The next day, we packed up our gear and hiked back to our car. The whole way back, we talked about where we would go next: the Eastern Sierras, Tahoe, the desert. My spirit was bubbling with optimism for the future and joy - emotions I hadn’t experienced in months. When we arrived back at our car, I knew that backpacking was going to be part of my life, no matter where I was. Even though I had initially encountered so many reasons not to do it, the experience made me realize I could do the things I wanted. And maybe that meant I could live the life I wanted.

This was just the beginning. Since that one trip in the Ventana Wilderness, I have backpacked all over Northern and Southern California. Each trip has been wildly different, and not all have gone as smoothly as my first trip. But at the end of every adventure, I still feel the same sense of joy and pride. Backpacking has taught me I can do hard things, and I will forever be grateful for that lesson.

Jini is the founder of Headlamp. She loves backpacking, climbing and paddling all over Nothern California. Her favorite place to backpack is Desolation Wilderness because of the many alpine lakes in the area!

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