The Journey of 7,400 Miles Begins with A Single Step
Calendar Year Triple Crown stories
May 6th, 2025
I took a few days off of working on the book to create a document on how one would resist a Russian military occupation in an alternate timeline where Russia was able to install their puppets into our seats of power and sow division within the US to destroy the country from within. I wrote about the blueprint that members of the resistance in this fictional universe would follow. You can read it in my SubStack here.
I wasn’t sure where to begin today. There’s so much to write about still. But I came across this video talking about Mark Twain’s writing process.
“The secret of getting ahead is getting started. The secret of getting started is breaking your complex overwhelming tasks into small manageable tasks, and starting on the first one.”
― Mark Twain
If I can claim to be a master of anything, I am a master of taking things step-by-step. Since 2016 I’ve hiked from Mexico to Canada three times and Georgia to Maine three times. I’ve ridden a bicycle from Mexico to Canada. I’ve hiked the length of Colorado, Arizona, and Vermont. I’ve hiked the length of the South Island in New Zealand.
Each of these trips seem impossible when you look at them in their totality. Hiking 2,650 miles from Mexico to Canada at two miles per hour takes 1,325 hours. If you break that up into 12 hours of hiking per day that comes out to 110.41 days. Add in town days and rest days you come right to the average of four to five months that most hikers take to hike the Pacific Crest Trail. To complete a Calendar Year Triple Crown I would have to complete each trail in around 90 days.
Think about everything you’ve done today since you woke up. Coffee, breakfast, your commute to work, working, lunch, pretending to work all afternoon, commuting home, making dinner, going to the gym, taking a shower, watching a show before bed. Think of how many different things happened in your day and how long the day feels.
Now imagine if your entire day, from the time that you woke up to the time that you went to bed, was spent hiking in the mountains. For some that’s the dream. For many, that would be a nightmare.
This was my reality for most of 2022. I would wake around 7am, take 15 minutes to pack up camp and then start hiking. Breakfast would be some cliff-bars or pop-tarts I’d eat as I walked. I’d take a half hour break for lunch and a 20 minute break around 6pm. Otherwise I would eat snacks on the move and keep hiking. I was so intent to keep moving I wouldn’t even take my pack off to collect water from streams. I would hike on after the sun had set every single day and set up camp between 11pm and 1am.
This is the schedule I would keep for 290 days. Literally climbing multiple mountains everyday. I hiked through waist deep snow and scrambled up and over ice-covered rock faces in New Hampshire. I suffered hypothermia during an ice storm in the High Sierra range and had a near brush with heat-stroke out of Seiad Valley in NorCal. Step by step I hiked like this as the seasons changed. Step by step I hiked through grizzly country at night in Yellowstone National Park. Step by step I hiked after I lost all feeling in my toes. Step by step by step until I had accomplished the seemingly impossible and become one of less than 20 people to ever complete a Calendar Year Triple Crown.
Calendar Year Triple Crown
Let me rewind and explain a Calendar Year Triple Crown. Most thru-hikers know what CYTC is but I’m guessing most readers won’t. A CYTC is completing the Appalachian, Pacific Crest, and Continental Divide trails in one calendar year.
The concept of the "Calendar Year Triple Crown" is generally attributed to ‘Flyin' Brian’ Robinson, who became the first person to accomplish this extraordinary feat in 2001. I first heard about the idea on my 2016 thru-hike of the Appalachian Trail. At that time I was struggling under my enormous 65L Osprey pack which consistently weighed 50+ pounds leaving town. I’d just gotten out of the Army the year before and had the stubborn pride that I was stronger than all these other liberal hippy hikers out here and took pride that my pack was heavier than theirs. This proved that I was strong, and manly, and tough. It had nothing to do with pride or ignorance or insecurity. Not at all!
It was true that I was exceptionally fit and strong. The year before I had deadlifted nearly 500 pounds. It was the strongest I’ve ever been in my life and I haven’t come close to that deadlift since. I had been a 240b gunner in the Army and that meant lugging around the unwieldy and extremely heavy weapon on our exercises. “Drill Sergeant, the M240B is a belt-fed, air-cooled, gas-operated medium machine gun that weighs 27.6 pounds and fires 7.62mm NATO ammunition at a cyclic rate of 650-950 rounds per minute! It has an effective range of 1,800 meters against point targets and a maximum range of 3,725 meters, with a muzzle velocity of 2,800 feet per second, Drill Sergeant!”
Mind you the 240b weighed 27.6lbs unloaded. Our SOP was to walk around with a 200 round belt loaded in the weapon on patrols. The two hundred round belt of large 7.62x51 cartridges weighed 9 pounds. 240 gunners are the most trigger happy people in the Army. Not because we’re more bloodthirsty than any other soldier, and not because we’re following our training to engage the enemy with overwhelming firepower when we make contact. No, it’s because the 240 gunner can’t wait to fire off as much ammo as he can, so that he doesn’t have to carry the weight on the long ruck back from the objective.
Then I’d have another couple hundred round belt of ammo in my pack. My assistant gunner, or A gunner, had the privilege of carrying the heavy tripod(imagine a big cast-iron skillet, except that it’s good for nothing, extremely awkward to carry, and you never use it) and an additional four or five hundred rounds of ammo. This is in addition to all the kit every infantryman requires. Kevlar body armor with ceramic armor plate inserts, a FLC fighting vest, a camelback full of water, food, rain gear, your PASGT helmet, night vision. The list was endless and none of it was ultralight. When you account for a full combat loadout with weapons, ammo, armor, and sustainment supplies each infantryman will walk around with between 100-110 pounds of crap, threatening to topple them with each step.
But of course your neck and back pain is never service related.
That was my mindset coming into the Appalachian Trail. I thought I was doing pretty good with only 50 pounds in my pack. I had the strength to carry this heavy pack but it was still a crushing load that made each mile grueling. I eventually worked up to 15, sometimes 20 miles a day. Each day, after only a few miles my feet would be throbbing with pain and I’d have to take 400mg of Ibuprofen every two hours just to keep going(another bad habit from the Army).
I was incredulous when I heard about a hiker who was attempting the Calendar Year Triple Crown that year. “No way!” Back then the idea of just walking from Georgia to Maine once seemed like an impossible task. But then to go on to walk from Mexico to Canada, and from Canada back to Mexico? And to do it at about twice the pace that I was going? “Impossible. It’s not humanly possible for anyone to hike that fast for that many days. I am the strongest and fittest person that I know and I’m struggling to make it 15 miles a day. No way anyone can hike 25 to 30 miles a day and keep that up for an entire year. Impossible!” Ah the arrogance of youth. Of course, if I couldn’t do it, then it was impossible!
My arrogance and pride will be a running theme in this story. I would go on to complete the Appalachian Trail after six and a half months. I would develop stress fractures in both feet and contract Lyme disease toward the end. Still, I finished and I didn’t quit. Two years later I’d go on to hike the Continental Divide Trail. I went into that trail thinking I was a hotshot seasoned thru-hiker. Oh yeah I’m a pro now. I’ve hiked the entire Appalachian Trail.
I had a whole new gear set-up. My 65L Osprey pack which weighed 5 lbs by itself was swapped for a 2.4lb 48L Osprey Exos. I swapped out my tent, ditched my pillow, and even got rid of my beloved Kindle e-reader and swapped to reading books on my phone. I’d gotten my pack down to 40-45 lbs leaving town(a significant improvement since you have to carry more food on the CDT).
You’re Not Ultralight Until Your Gear Takes You to the Brink of Death
It was on the CDT that I learned what true ultralight hiking looks like and learned how to hike 30 miles day after day. I’d never seen a trekking pole tent until I saw my friend FlyBy setting up her tiny space-ship looking tent. “That thing only weighs ONE POUND? Hmm, maybe I should get one. Ah, it costs $700? Well, maybe not.”
Flyby and I hiked by ourselves through the Great Divide basin, we’d lost the rest of the group that we’d hiked with through Montana. TomTom, Will, and Heather had gotten off trail to go back to their regular lives. B was still on trail and intent on finishing the whole thing, but just disappeared one day and never re-joined us. I’m still not sure if we offended B or he got tired of hiking with us or what happened. And being the strong men that we are neither of us ever broached the topic and just pretended like we were strangers and that we hadn’t just spent two months hiking together.
The Basin is a stark, sweeping high desert landscape in southern Wyoming. It’s aptly named because it is a massive, arid basin where water neither flows to the Atlantic nor the Pacific, but instead evaporates or seeps into the ground. You just hike along old forest service roads through this remote section and will routinely have to do 20 to 30 mile water carries. You’ll see the same view day after day: sagebrush plains stretching to the horizon topped by a blue, vast, cloudless sky. The roads that you follow will continue straight as an arrow literally to the horizon without any other interesting landmarks. In the summer the heat can become unbearable and there’s always intense sun exposure owing to the lack of any trees for shade.
During that stretch Flyby and I took great pleasure in reading the log-books whenever we came across one. There wasn’t much else for entertainment in that vast expanse of open plains dotted by curious little antelope heads which would track you as you walked and darted away as you got too close. Did you know that the population of antelope in Wyoming outnumbers its human residents? Pronghorn antelope, which aren't true antelope but unique North America, are native to Wyoming and the western plains.
We kept coming across entries by Didgeridoo and Hotlegs. I thought for sure these were two quirky older women by their names and entries. I was surprised, and a bit disappointed to learn that they were two young men in their early 30s when we finally caught up to them in Leadville, Colorado. Didgeridoo had married Hotlegs’ sister and that was how they’d developed their bond. They’d gone through paramedic school together and hiked the PCT together. They were now on the second leg of their triple crown.
Didgeridoo was ultralight. He had the tiny pack and trekking pole tent and all of it. His base weight(weight of his pack without food and water) was definitely under 10 pounds. Hotlegs was stupid ultralight. He had a tiny tarp. His sleeping pad was a super thin foam mat that he’d cut to be just long enough for his torso. People often mistook him for a day-hiker because of how small his pack was. He would buy one pair of dress-socks from Walmart when we got to town and wear them for a week or two until they got holes, then buy another pair in the next town. He didn’t carry any extra socks. Or underwear, or shorts, or anything else. His pack weighed 6 pounds six ounces. I’m not kidding. He was super proud of his ultralight set-up.
I say Hotlegs was stupid ultralight because his lack of adequate cold weather gear might have killed him in Colorado if we hadn’t been there to help out. It was late September and we entered the San Juan range leaving from Lake City, Colorado.
The San Juan range is considered the most wild and challenging section on the entire Continental Divide Trail. Most of the trail through this section is above 12,000ft and there’s many sections where you’re just walking along a narrow trail on the side of a steep mountain with sheer steep drop-offs that would send you into the abyss. We all knew that this would be a harsh and exposed section and FlyBy and I had had several conversations about how we would take an alternate route around the San Juans if bad weather was on the forecast.
“Yeah I really don’t want to be caught up in those mountains if the weather is going to be nasty.” I said as I trudged along, my footsteps kicking up little puffs of orange Wyoming dust.
“Me either, that sounds really dangerous.” Said Flyby. Her voice light and musical.
“It’s already starting to get cold, imagine if we got caught in some cold rain up at altitude.” I said, not sure if I was trying to convince Flyby or myself.
“Yeah man, I’ve hiked in Colorado before and the weather’s no joke!” Flyby was always very supportive and we tended to both not like to take big risks. That was why we were able to get along so well and hike together for 1,900 miles.
We worried so much about the San Juan range because we knew we would arrive there in late September which is when the weather window closes for that section. The San Juans become dangerous and impassable to the average thru-hiker once the first big snows of the year have set in. The section is 120 miles long and takes most people about six days in the summer. In winter conditions you’d need to carry 12-14 days of food and have snow shoes, crampons, and ice-axes and even then some of the traverses would be dangerous. Avalanches would become a very real concern.
Flyby and I both knew we were not skilled or equipped to deal with such conditions. The moment of decision came in Lake City, Colorado. From there we could either turn and take the Creede alternate, a lower elevation route that passes through the town of Creede, Colorado or continue on through the rugged San Juan mountains. The Creede alternate is the route most northbound hikers take as snow levels in the San Juans make it impassable from May into June most years. The forecast called for highs in the low 50s and five days of freezing rain and high winds in the mountains.
“Oh Flyby I don’t think I want to be up at 12,000 feet with that much rain and wind on the forecast.” I told her, seeking assurance.
“I agree I think we should probably take Creede.” She responded.
“Come on you guys, the San Juans are the best part of the CDT. You can’t miss it! We’re all going, you have to come!” I don’t remember if it was Hotlegs or Didgeridoo that first started on us. It doesn’t matter. Within moments the whole crew was piling on with the peer pressure. Flyby and I eventually caved and followed the group into the San Juans against our better judgement. Humans are tribal animals and it’s hard to go against the wishes of the tribe, even when your gut is screaming at you that to walk into the San Juans with five days of freezing rain on the forecast is a deeply deeply stupid idea.
Thanks for reading. Tune in tomorrow to read about our misadventure in the San Juans :)
I’m enjoying your CDT stories. I only started following you on YouTube when you were on the AT. Keep writing . . .