Backpacking Into history

History will be made soon. Our ambassador Caelan Dobbs is on track to be the first transgender individual to complete the US thru hike Triple Crown. (This consists of thru hiking the Appalachian Trail, the Continental Divide Trail, and the Pacific Crest Trail.) They, along with their partner Lyla Harrod and dog Truman, are about 2/3 of the way done with the PCT at the time this is being written. While walking toward history, Cal is also raising money for The Trevor Project and inspiring their students back home. 

Lyla is hot on Cal's heels hoping to be the second trans individual to complete the Triple Crown. Once the trio completes the PCT, Lyla will head off to the CDT to complete that. Both previously completed the famed AT and have more distance hiking objectives to look forward to in the future. 

We sent them off on the PCT with Aircontact Lite 35+10 SL and despite some crazy snow in the Sierras things seem to be going well. Let's get to know Lyla and Cal a bit more.

Lyla, Truman, and Cal at the start of the PCT

How did you get into backpacking/hiking?

Lyla: I moved to Seattle after graduating college and had a friend who brought me on day hikes and backpacking trips in the Cascades. The staggering beauty, and chance to connect with nature in a more intimate way was deeply appealing to me. For years after, I developed my skills on backpacking trips and explored public lands around the country as well as finding peace and connection in the woods right by where I ended up living in eastern Massachusetts.

Appalachian Trail marker

Caelan: I was born and raised in the concrete jungle of Los Angeles, CA. While I spent my summers at the beach, my family didn’t have the time or resources for “outdoorsy” activities growing up but I always craved adventure.

I competed in cross country and track throughout high school and college but throughout my many years of playing sports I hadn’t even heard of backpacking until the second semester of my senior year of college when a friend invited me on a backpacking trip to the White Mountains of New Hampshire. He told me the trail we were hiking crossed the Appalachian Trail but I had never heard of it. When he explained that it was a 2,200 mile trail from Georgia to Maine I said, “I’m doing that after graduation,” which at the time was a month away. 

Cal in the snow


I rescinded my job applications and my friend helped teach me what I needed to know and one month later I began my northbound Appalachian Trail (AT) Thru hike in the summer of 2018. 


There was a steep learning curve but my personal journey to discovering my love of backpacking is important because it shows that you don’t need prior experience to be able to enjoy the outdoors. People who see the things I do now assume I must’ve grown up doing this but that couldn’t be further from the truth. Everyone belongs outdoors in whatever capacity they feel most comfortable and passionate about.


How has the outdoors helped you be your most authentic self?

L: In the early stages of my gender transition, hiking was my refuge. In the solitude of the woods, I could wear whatever made me feel good and I could let my guard down emotionally. The woods became a trusted friend, so I never feel alone when I'm outside, even deep in the backcountry. 

Lyla excited to be on the trail

Years later, I still find authenticity comes easily to me in the outdoors. Through struggle and experience, long distance backpacking is a unique way of stripping yourself down to the core and building yourself back up, and I couldn't be prouder of who I've become. 

C: My relationship with the outdoors has everything to do with who I am today. My time in the wilderness has allowed me to be free and flourish but it has also taught me new skills and grow in new directions. 

 Backpacking has given me time to consider and cultivate the person I want to be independent of society’s mirrors and expectations. I get to play with my inner child when I’m outside and explore the facets I must contain in my professional and personal life. As a transgender person I feel safest when I’m outside because I can exist in my most holistic form independent of pressure to fulfill a label or fit into a box and without other peoples projections of who I should be and how I should act.


Nature doesn’t shame anyone and being free of the shame society teaches us for the ways we are different is liberating. I love myself most when I am among the trees and mountains.  


What is your favorite thing about being on the trail for so long?

L: Long distance hiking offers immersion into both the wilderness you're walking through, and the culture of the communities you spend time in. Shorter backpacking trips don't allow you to "settle in" as much, since they're over by the time you're finding your rhythm and plugging in to your surroundings. Spending months in the outdoors, I find I'm attuned to the world in a way that I tend to lose once I'm back in "The Real World", and that feeling is difficult to replicate.

C: Thru hiking is not for everyone. It is a long-term time and financial commitment. It’s a tremendous sacrifice to take five or six months out of your life and walk from one side of the country to the other. What could possibly possess someone to want to do this? Why not just do a section hike for a week or a weekend backpacking trip? 

To me, it’s the difference between visiting a place and making it your home. The mountains are my home and you don’t visit your home - you live there! 


I feel most at home with my belongings on my back walking as far as I can each day. I feel most fulfilled making steady progress toward a goal and enjoying all the beauty and abundance that surrounds me along the way. I do not personally view completionist thru hiking as an event but rather walking itself as a daily meditation and act of love necessary to my wellbeing.


The longer the hike, the bigger the growth is when you invest intentionally in the journey. You can’t plan a thru hike because there are too many variables so it’s a good lesson in taking things one step at a time and letting go. I love creative problem-solving and I love immersing myself to the fullest extent. To me this is only possible when spending months on trail. 


Best spot on the AT for someone to do a day hike? 

L: Grayson Highlands! I'm an animal lover and Grayson Highlands in Southern Virginia is a gem not only because of the gorgeous open meadows, but also because of the wild ponies that reside there. They're beautiful, silly, and friendly and it makes for a magical experience!

Harper's Ferry

C: Smoky Mountains, Grayson Highlands, Shenandoah, Harpers Ferry, Delaware Water Gap, Mt. Greylock, Killington, White Mountains 


What are your post Triple Crown Plans?

L: My partner, Caelan and I will likely hike and travel around a bit while we start to scheme our next big adventure! During that time however, I plan to continue developing a scholarship with my friends at The Venture Out Project for future transgender thru-hikers to reduce financial barriers to thru-hiking.

Truman the trail dog

C: More hiking! As long as I have money I will continue to hike but I do miss my profession as a high school teacher and track coach. I’ve stayed in touch with many students over the course of this journey and they told me how much it meant to watch their teacher hike to become the first transgender Triple Crowner. I think young people learn as much from direct instruction as they do from modeling so I hope I continue to do both in the future. 

The nice thing about teaching is there are always winter and summer breaks. I plan to use mine to hike more trails.


Something you wish you knew before you started thru-hiking.

L: You can do even more than you think. I love to push myself as a hiker and backpacker because more often than not I find I'm capable of achieving my goals. As you get stronger and more confident in your abilities, you'll be able to take on challenges that would have seemed impossible not long before.

So much snow in the Sierras

C: I wish I knew that not everyone is on trail for the same reasons. When I hiked the AT I assumed everyone was on trail with similar intentions to me – to challenge themselves, find themselves, to connect with nature, to heal, etc. The unfortunate reality is that not all everyone on trail will make good friends or have your best interest at heart and I wish I would have known how to advocate for myself better. 

During my first thru hike I found myself sucked into other peoples hikes but because I didn’t know that I was allowed to set boundaries or hike on I stayed in situations that were not consistent with my intentions on trail. 


There's a phrase on trail “hike your own hike” and I learned that the hard way.

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