Written by Jason Lessley, the first finisher of the 2021 Oboz Trail Experience: Bozeman. He completed the 17 trail segments totaling just over 56 miles in two days.

To start, I’m not any sort of athlete, avid trail runner or anything like that. I’ve never done or attempted a 50-mile adventure or a 24-hour challenge. I’m just a normal guy who likes the outdoors. I like to play outdoors whenever my schedule and body allow. I do however, do things on occasion, once a year or so, most would never consider. Challenging myself, and coming out of it with great experiences and stories. From attempting to summit the Sphinx on New Years Day, backpacking the Narrows up then back down in the middle of winter, 3-day backpacking trip in the jungles of Guam pushing my physical limits way past where they had been before, pack rafting a few bodies of water along the way. All great stories now, but crazy adventures at the time. I’m also the President of a non-profit organization centered around the outdoors for combat veterans with PTSD or TBI. I believe the outdoors has amazing healing properties, and it’s what has kept me going.

It all started on an email received from Oboz on July 22nd, (apparently overlooked the June 12th email) about the Oboz Trail Experience 2021. Never heard of it, and after opening the email and a quick skim over, I saw that I already planned on being in Bozeman during the dates of the event, August 6th-15th. Oh man, I haven’t gotten to hike and explore Bozeman in forever, well 21 years to be exact. I’m doing this!

I’m 45 years old, been a resident of Montana for 45 years, my family is at least 7 generations deep from Montana, maybe more. In fact they started homesteading here in the late 1800s on one side of the family. The other side of the family, well our family name is on the Bozeman Law and Justice Center, “Lessley”. My roots are deep here. How have I not been able to explore and hike Bozeman for the last 21 years? I’m active duty military, part of the Navy’s elite Search and Rescue teams, and am in the process of retiring and moving back to Montana. Being active duty military, I was able to keep my residency and would come back to visit about once a year and see family.

I sent the Oboz email to my sister who now lives in Anaconda and told her I’m doing this. Just doing the challenge was not enough though. From the Oboz email it said “push your limits” and in the FAQs on the web page said “We encourage people of all abilities to sign up and challenge themselves”. Those two phrases were the catalyst for what was about to come. Push my limits, and challenge myself, consider it done. Well, two immediate thoughts came to mind. Either I am backpacking this event from trail to trail carrying 9 days of supplies or I am doing this event start to finish without stopping, driving from trailhead to trailhead. The latter ended up being my choice as the backpacking seemed like it had some logistical challenges, like where was I going to legally sleep? The city would probably not appreciate me setting up camp at Peet’s Hill one night and the “M” the next night. “All in one shot, that was doable. 40.17 miles, I can do that,” were the thoughts going through my head.

I was in San Diego, California at that time and after the initial discussion with my sister, I did not put much more thought into it as I was scrambling to finish up home improvement projects on my house before it went on the market late July. I hit the road for Montana with the first truck load of my possessions on July 31st and arrived in Bozeman on the 1st. I started to strategize how I was going to attack this challenge. Did some map study, distancing, driving, timing and quickly realized it was going to take more that 40 miles to complete. Some of these routes are 1-way and I have to get back to my car, some trails were segments of trails so I had to do some hiking to get to the segment. My rough math came up with 55-60 miles. This made it more challenging than the initial thought, but I still decided it was doable. On August 3rd, I did some trailhead scouting to make sure I knew where to drive for all the trails and not waste time driving during the challenge. I ended up doing some trail running on a few of the trails. That was a spur-of-the-moment decision as I had not made time to hike, run or do any sort of physical training in at least 3 months. I figured I should probably run to see how I would do at this elevation and with no cardio for 3 months. I ended up doing an estimated 10 miles of trail running and it really boosted my moral and confidence. I was just scouting and goofing off and in just an afternoon had visited all of the trailheads (but one, more on that later) and had run 10 or so miles. In my head I knew I had this! The day prior to the challenge I filled the car with all the food, clothes and supplies I thought I would need. Then I put all the trails on my phone in the order I would complete them, minimizing driving time and doing the harder ones during the daylight and easy ones during darkness. 

After getting them all in my phone in a checklist, I counted them. 16….there were supposed to be 17 trails, why do I only have 16? I had done my route planning by looking at the map on the website, then getting the name from the list below the map. After going down the list on the webpage and comparing it to my notes, I discovered I had missed Storm Castle Ascent. It was so far away from the others and hidden at the bottom left of the map, I had missed it. I had decided I could just tack it on the end and it would be fine. The initial plan was to have my sister as a support team with me. Able to drive me around, save me from doing more miles than needed, and allow me to crush calories on drives to trailheads. That did not happen though as she had other life commitments that did not allow for the time needed.

Challenge day started well. Got plenty of sleep, nutrition and hydration the day prior and felt great, ready to rock! I started with Saddle Peak as it was one of the more difficult ones and the drive was out of the way. (So I thought, before my Storm Castle, oops) I got to the trailhead at 1130 and waited till the clock struck 12 and started the journey. Well, actually waited till about a quarter after to make sure I did not jump the gun and the hike didn’t count. My goal was a steady hike speed of 2mph. I figured with that speed, my endurance could last and I would not burn out and could complete by sunset on the 7th. I figured I could do the flat level trails at 4mph. 

The Saddle Peak hike was great. I loved all the water crossings, the meadows, wild flowers, and the views were spectacular. Even though I was on a timeline, I definitely made time to stop and enjoy the sights and sounds. The last mile and a half caught me a little off guard on the steepness and was definitely slower than I had planned. All good though. When I was on top, it immediately gave me flashbacks from prior to leaving for the military. I had done the ridge run many times, and had actually done it for training prior to going into the military. Search and Rescue had very high standards for physical fitness to be accepted so training was a must. Being back on that ridge uncovered those memories I had forgotten about for decades. I took it slow coming down off the peak and picked up the pace on miles 7-9. I got to the bottom and knew I was behind my timeline. Too much goofing off, enjoying the scenery, or too slow up the steep summit climb. Either way, I’d figure I’d make it work. 

The second hike was supposed to be Baldy Mountain, but I audibled and skipped it. My thought process was I would be pushing sunset on the way down and would rather not be coming down that mountain in the dark. I skipped it and went to Drinking Horse. Another great trail with great views, I sat at one of the benches for a few minutes just staring at the beauty around me thinking “this is the life, I’m glad I’m back home.” 

Trail 3 was the “M”. This is a trail I used to run up and down as a kid and again for training before joining the Navy to qualify for the Search and Rescue program. The route up was uneventful, pretty exhausting, but tolerable. Again flashbacks from my childhood, memories of training, and memories of a visit a few years back climbing the hill in the winter with my mom, sister and daughter with crampons. It was sunset, so I stayed up there to enjoy that; well worth it! The route down did not go so well.

In October 2013 I had a life threatening injury occur during physical training in the Navy. A complete knee dislocation, torn ACL, PCL, MCL, LCL, patellar tendon tear, impact fracture to the tib/fib and femur, and the list goes on. Three surgeries later and several more needed but never done, and my knee is in its current status. PCL was intact enough to leave alone, ACL was replaced, no MCL or LCL and both meniscus were unsalvageable so removed. My knee will never be the same, and if the doctors had it their way, I would never do the things I continue t do. I continued in Search and Rescue and jumping out of helicopters until my retirement, though there were many battles to get and keep the medical clearance to do so.

Anybody who knows anything about hiking, running, backpacking, trail running etc., knows downhill is a knee killer. Well, within 5 minutes of beginning my descent of the “M”, my knee immediately decided it was done. Every step, an ice pick was stabbing my knee. After finally getting to my car, I contemplated my options… well, option. I was completing this challenge, the questions were how was I going to do that. I decided I would push through it. 

It was dark now and the night trails were all easy, relatively flat and should be able to be completed, even if I hobble with a limp all night long. I knew my aspirations of 24ish hours were out the window as the night trails were all planned on being run at a 4mph pace or 15 minutes per mile, and now I would be moving at sloth speed. Oh well, life gives you challenges, figure it out. 

Trail 4, Story Mill to the M trailhead. Since I was rolling solo without support, that meant the M to Story Mill, and then back to the M. I threw on a headlamp and lights on the shoes and hit the trail. Growing up, I do not remember that path being there. It’s nice and I’m glad it was put in. It seems great for walkers, runners, and bikers. I started off walking, probably more like hobbling. Really focused on long strides and good mechanics with that bad knee. I wanted to try to use that hike as a stretch session in hopes I could salvage my initial goals. I was able to wince a few light jogs along the way, but they were short lived. The ice pick would not go away. I don’t recall where my mind went, but clearly was not on the trail. I remember hearing loud music and wondered if it were coming from a trailer park nearby I used to go to parties at as a kid, or if it was the Filling Station. Then my thoughts descended from the clouds and realized if I’m almost to the Filling Station, I had way over shot the turn around spot. More time off the clock, and more miles added. I ended up doing 5.78 miles total when it should have been 4.6. 

Trail 5 was Bozeman Beach. This place was in its infancy when I left the military, and I don’t think any of the trails were there. I was not sure what kind of pace I could keep on this trail. I had about 20 minutes to midnight and was not sure if the time finished after midnight, if it would count the trail as complete, as I would have finished on a different day than when I started. I took the 20 minutes to hydrate, slam some calories, and stretch-out the knee. At 1202 I kicked off and was able to keep a decent paced, long-strided walk, but still slower than planned. 

Trail 6 was Snowfill. I’m glad I scoped out this trail ahead of time because there are trails all over and at night would have taken longer to figure out which one to stay on. Again tried to keep a decent walk pace. There was more elevation than the previous two hikes and though very slight elevation, that downhill was excruciating. I was able to keep at 2mph, but if there was anything steeper down, I was confident I would not be able to manage. 

Trail 7 was Harper Pucket. I parked in a pull-off in a farmer’s field and refilled my water bladder on my hydration vest. At this point it is nearly 2am on Saturday morning. As I’m filling up my water, a vehicle slowly drives by and stops. I know it’s 2am on a weekend and they are thinking nothing good is going on at 2am on a Saturday in the middle of nowhere in a farmers field. The window rolls down and a polite but questioning “is everything ok” from the driver is said and I reply with “yes, just going for a little run”. A strange look, the window begins to roll up and the car slowly drives away. I can only imagine what they were thinking. This hike like the previous few was uneventful, nothing to see in the pitch of dark, but again flooded my mind with childhood memories. My mother lived on Hidden Valley and this hike took me right past her house. 

Trail 8, I headed to Peet’s Hill. Here, I iced my knee with instant cold packs I had on hand as the swelling was very apparent. I set a timer for 30 minutes and took a quick cat nap while the knee took in the cold. 30 minutes later the alarm goes off and I saddle up. I start with Gallagator, another short dark uneventful stroll, then off to trail 9, the trek to Schnee’s. 

I don’t remember this path to Main Street when I was a kid, but this hike took me down memory lane once again. I daydreamed of playing in Lindley Park as a kid and remembered a hand drawn picture of me I have from one of my parents’ friends. I was probably 5 or 6 years old at Lindley Park playing with a bicycle tire, spinning it on the bike. I still have that 8x10 drawing framed. As I navigated the path I had to move some Sweet Pea gates they had set up. I had forgotten all about the Sweet Pea Festivals here. Then the walk down Main Street. Quiet, serine, and only a couple city workers present setting up road closed signs for the festival. 

Trail 10, Peet’s Hill. Again, floods of memories during this hike. I mean, Peet’s Hill as a kid, I’m not sure how I did not break a bone. From dirt biking down the hill as fast as possible (helmets were not a thing then) to sledding down the hill. We used to take the trucks off our skateboards and snowboard down, pretty sure that was before snowboarding was a thing. I can’t count how many times I had the breath knocked out of me on that hill, or smashed into the structure that used to be at the bottom of that hill. Well, hiking up the hill was good, and the sun was just starting to peak up over the Bridgers. Sunsets are pretty good on Peet’s Hill; I think this was my first sunrise on Peet’s Hill though, it was also enjoyable. That last 100 yards down Peet’s Hill to the car was not so enjoyable. That was the steepest decline yet since my knee was aggravated on the M. I really wanted a Toradol Injection, or even just a Cortisone injection, anything to get me by. With Bozeman now starting to wake up, I took an unplanned detour. I drove to Walmart and picked up more instant ice packs since I used what I had brought, but more importantly I grabbed an off the shelf knee brace. I was not sure if it was going to help, but I knew it was not going to hurt.  

Off to trail 11, Painted Hills. Armed with a snug wrap of an ace bandage and a cheap knee brace, I was on another great trail and it was early enough that I was only one of two cars there. Here, my pace slowed from the previous level terrain trails. There is not much elevation change there. In fact if you would have asked me the day prior, I would have told you zero change. It was so little it should not matter or affect anyone. This day though, taking a single stair down was pure hell, and I was dreading those switchbacks something fierce. Great scenery and a slow pace, I enjoyed the hike. I was probably passed by a dozen hikers and runners. I’m sure they were either thinking this cripple needs to get off the trail or good for this guy rehabilitating himself. When those switchbacks came, they were everything I had anticipated. Pure and absolute hell! I kept reminding myself this was not even close to the worst pain I’d encountered. I was reaching for ways to overcome that stupid knee, but the knee was not having it, it wanted to win this battle, and boy was it putting up a fight. That short 3.5 mile hike was grueling, and I could not help but think what was I going to do on Baldy Mountain, and Storm Castle? I should be nearing the peak of Baldy at this time followed by Storm Castle. Those thousands of feet of elevation gain loomed in my head, actually the descent loomed in my head. Then the hours I was behind, the many hours, the mental edge of “I got this” was starting to slip. I kept pushing on, though. 

Trail 12, Highland Glen. More dreaded terrain, laughable terrain, but dreaded. For two miles, only a few thoughts crossed my mind. Thought One: when I get to the end, should I call a cab for a two-mile ride back to my car? Thought Two: I wonder if Bozeman Deaconess Hospital on the other side of the field would give me a Toradol or Cortisone injection, no questions asked. I did neither and made the 4.12 mile hobble. Oh, and Thought Three: I wonder if these cows are going to let me pass peacefully. 

Trail 13 on my list, Triple Tree. I sat in my car at the trailhead contemplating skipping this and doing Sourdough next. I decided since I was already there, just to do it. Turns out Triple Tree was the breaking point. My pace slowed another 10 minutes/mile and it felt like eternity. I kept looking at my Garmin to see how far I had gone. It felt like a mile had passed, but a glance at the milage revealed 1/10th of a mile. It was nearly 4pm on Saturday when I finally completed that trail. Every ounce of moral was sucked out of me, every step was miserable. I knew I was not physically able to do Baldy or Storm Castle, but I could have done River Road and Sourdough. Triple Tree broke my mind, my knee had won and I threw in the towel. I knew I was not done, my fight was not over. I knew I was getting all the trails done, not in the 24ish hours I had set out to, but they were getting done. I drove to my dad’s where I was staying and sat in that driveway for probably an hour. I wanted to do this straight through. I thought, maybe I sleep at the next trailhead in the car. That’s a close second right? That debate with myself went on. I knew I just needed a day or two off of the knee and I could finish up easily. Looking back at all the trails completed so far, I knew I could have made my goal and it infuriated me that I didn’t get it done. I decided a bed with good rest was the way to go and not curled up in weird positions in a car at a trailhead. From my years of knee rehab experience, I knew my knee needed to be straight; if it was left bent for hours sleeping, it would be locked and so stiff, not able to straighten out again. I fashioned a splint to keep it straight all night and went to sleep. No shower, no changing or removing clothes, my shoes did not even come off. I didn’t finish my goal or the challenge, I did not deserve any of those luxuries. 

After 28 hours of straight hiking, 43.4 miles, I slept like a log. I woke up, and the first thing that crossed my mind was, how is my knee. I laid there on my back with anticipation, and probably some fear. I slowly raised my leg off the bed , removed the splint and slowly started to bend the knee bringing the thigh to my chest. No way, I thought to myself. I looked at it, the swelling was not bad, not good either. Zero pain, no discomfort. I did it several more times in disbelief. Then got up and walked around. This never happens, when my knee was screaming that much in the past it would take days if not weeks to be good, and this time in 12 hours? My moral was back, adrenaline was flowing, I was doing this. I told myself it was too good to be true and I was going to take it easy and only do one of the hard trails today and do the other one tomorrow. 

I headed right to Sourdough and started that trek. 6.6 miles with a very low grade elevation gain. This was the test to see if I should attempt Baldy next. Sourdough was busy as it always is in the summer on a weekend. This was also the last trail I ran before flying off to the Navy. More memory lane. I walked up with no issues, a slower pace but on par with the previous day’s hobble pace on flat terrain. I reach the 3.3 mile point and turn around. Now the test, how was the downhill going to go. To my surprise, well. Very little discomfort and I was able to keep the same pace on the way down. Things were looking up and I thought, ya know, I think I will just finish all the trails today, I’ll probably be pushing dark on Storm Castle but that's ok, and River Road is fine at night. I'm doing this, I'm finishing today! I put “Cant Hurt Me” on audiobook and decided I was listening to this the rest of the day. That book motivates me and reminds me how weak my mind and body really are and to keep pushing. 

Off to Baldy Mountain, and by way of my now mortal enemy, the M steep way up. I’ve never cursed at a mountain, but when I arrived that morning, I cursed up a storm and said I will own this mountain today. The mountain had different plans though. It was sort of a struggle going up, the first mile pissed me off. My Garmin watch beeped and buzzed so I knew I reached a mile marker. I had thought it had been two miles because it had felt long and hard. I look down and it was only one mile. Another volley of curses fired at the mountain. A slow steady and mildly painful pace took hold from here on out. I was focused on the audiobook; so good, so motivating. I took in the burnt landscape from last year’s fire I had heard about from friends and family as it happened. I remembered running this trail 20-30 years ago. This time I was the tortoise and not the hare. It took four hours to get to the top. I chatted with an airline pilot who was there about to hastily make his way down. I took a couple salt tablets and GU and washed them down with the last of the water in my front water bottles. I open my hydration pack to swap out the empty bottles with the last litter soft bottle…except it was not there. I specifically remember filling it up at the car, did I not put it in my pack? The thought of four hours without water was daunting. Chalk another one up for the mountain. Also, if it took four hours to get down, most of Storm Castle was going to be in the dark. I didn’t like that idea either. On my trek back, I tried to pick up the pace. The real steep and technical parts were not having it, though. They were making my knee scream. The lower downgrade and flats I was able to trot. I figured the faster I get down, the less time without water and the less hiking in the dark. I was faster, but not much getting down the mountain in 3.5 hours. I get to the car and sitting on the back bumper still is that 1 liter of water. 

As I am driving to Storm Castle, I know I’m only getting half way up that mountain before it’s dark. It was not really a trail I wanted to do in the dark, but oh well. I was feeling good and this was happening. Halfway to Four Corners, it starts pouring rain, then thunder and lightning. Well that’s a game changer, those are more variables than I was willing to deal with. Instead, I head to River Road and sit out the storm waiting for a break so I could knock out the 2 miles. The break did come and it was right at sunset. I jumped out and began to trot down the road. It was not a real jog, but it was the best I had done in the last day or so and I got it done. Just in time, too, because the next wave of thunder and lightning rolled in. I figured that was a sign and I should make my Storm Castle attempt in the morning. 

Trail 17 of 17, Storm Castle did not disappoint. The name did not sound familiar and I was not sure if I had ever done that hike. I arrived early enough that I was only the second car there. I headed up the trail and liked the steady incline of the trail. Not too steep but still a good climb. I figured I had all day so took a couple of detours of lesser traveled trails to see where they led, and then would go back to the main trail. The views on this trail were phenomenal and I was already making plans in my head to go back with my camera equipment. I reached the top and threw both arms over my head claiming victory. 

While I did not do the challenge in my original 24-hour timeline, I completed it, and completed it with purpose and heart. A few selfies and pictures of fat, overfed chipmunks later, I realize I have cell service. Since this was a one-way hike, I immediately stopped and saved the hike on my Garmin so it would register me complete with the Trail Experience. 

I could officially chalk this up as another crazy experience I put myself through. 17 trails, 56.56 miles, 3 gallons of water, 8 bottles of gatorade, 8 bananas, 4 peanut butter and jelly sandwiches, 4 Taco Johns burritos, 8 Larabars, 30 salt tablets, a little bit of suffering, and a lot of memories.