The Triple Triple Story – Written by Matthew Fairbrother

The North Shore of Vancouver has long been a proving ground for mountain bikers, a wild, untamed labyrinth of steep technical descents and iconic wooden features. It’s where the sport was reshaped, as riders took to the forest with chainsaws and raw ambition, carving trails that defied physics. The roots of freeride mountain biking run deep here, born from a mix of necessity and creative defiance. Slick, moss-covered rock faces, technical singletrack, and narrow skinnies are all part of the North Shore’s DNA, demanding both skill and nerve from anyone daring to test themselves. For decades, legends have been forged in these woods.

From the early pioneers who rode rickety structures and gapped cliffs to modern-day shredders pushing the limits of what’s possible, the North Shore is where mountain biking transcends the ordinary. The forest itself feels alive, its ancient cedars standing sentinel over those who pass through, whispering tales of triumph and humility alike.

For years, I’ve obsessed over videos of riders tackling these legendary lines, each edit more jaw-dropping than the last. The idea isn’t just to ride the Shore but to leave my mark, to etch my name into its storied history. Like those before me, I want to prove something, not just to the forest or the bike community, but to myself.

The idea struck me during a late-night scrolling session, watching yet another rider crush the infamous Triple Crown, a gruelling feat that strings together the tops of Mount Fromme, Cypress Mountain, and Mount Seymour in a single ride. But I wanted more. What if I pushed it further? What if I attempted the Triple Crown three times in a single, continuous effort? The thought seemed absurd, but it also burned with the promise of a challenge worthy of the North Shore's Mystique. More scrolling revealed Anthony Boussetta successfully tackled this route in 2021, the challenge was on. It was possible.

To prepare for such an undertaking, I needed a guide, someone who knew the trails along with their nuances. Enter Celeste Pomerantz, a rider who learnt to ride a bike on the Triple Crown route, and ever since has used it as a playground to pave her path. Celeste’s deep knowledge of the terrain and infectious energy made her the perfect partner to show me the ropes and, hopefully, keep me grounded as I set out to etch my mark on these legendary trails.

The unique thing about the Triple Crown is there isn’t a hard route, It is up to your interpretation as long as you ride the highest trail on each of mountains. With Celeste’s guidance and a month dedicated to learning every trail on the North Shore. I rode and timed every variation, weighed up how much effort each track took compared to another, and in my eyes crafted the perfect route. I was looking for efficiency and fun whilst ensuring I kept true to the North Shores routes. It’s not often I’m lucky enough to get this lost in a process, to me, there is no better feeling than being completely tunnel visioned by this one goal and doing everything you can to set yourself up for it. After a month of being engulfed by this process I was feeling confident and ready to put my body to the test.

- Rock armoured trails...a north shore special. These proved to be a challenge for Matthew in later parts of his ride...especially at night.

06:00 - The Start

I opted for a laid-back start time, starting at 6am gave me enough time to fit in 8 hours of sleep and still have a full day of light. The plan was to attack the first two-thirds of this ride, to make the most of the daylight and my mental sharpness and for the last third, well there wasn’t much of a plan, I would just have to suck it up and deal with the consequences.

I camped out in a U-haul van overnight just up the road from Deep Cove. I woke up at 5:50 am and was down at the end of the pier ready to start by 6 am. I was rather stoked with my efficiency despite a rough night's sleep.

- Heading out at first light. Doesn't get better than this.

I dipped my tyres in the water, a classic North Shore Triple Crown ritual and then I was off. There was a self-induced buzz in the air, there’s always a huge build-up before a ride like this and once you get there, there's a drastic switch from the pressure of nerves to the rush of adrenaline.

- Dipping his tires in the cold ocean water.

Not even 5 minutes in I had my first reality check. While riding through a park on the way to Mt Seymour Road I heard something rustling through the bushes. As a Kiwi this was my worst fear, at home in New Zealand there's very little to be afraid of in the words. I turned on my headlight and started looking around, eventually finding a set of eyes staring down at me. It was a Coyote, I let out a slight sigh of relief, but I wasn’t going to let my guard down.

08:05 - ⅓ Triple Crown Completed

At this point was still trying to convince my body to wake up, I’d had a slow start, my legs were turning but they didn’t exactly feel good. The body still needed some time to come alive. I was keeping on pace and was greeted at the top of Mt Seymour by a vibrant sunrise. The descent I chose was a solid mix of classics and efficiency, from the top I’d ride CBC, Cabin Trail, and Ned’s Atomic Dustbin. It was important to me every run held a strong North Shore essence, without sacrificing my personal preferences, I think this lap was a perfect fit. The dirt was crisp, a classic North Shore hero dirt day, excitement was high and by the time I got to Ned’s Atomic Dustbin, I’d let the brakes go and I'd finally woken up. The tone for the day had been set, how sick are bikes?!

First mountain, Seymour, Done.

12:35 - 1 Triple Crown Completed

By the time I hit Mt Fromme my body was starting to kick into gear, at this point it was still a normal ride, I like to keep my mind from looking far ahead. I’d convinced myself Mt Fromme was only a small hill, and in comparison, to Seymour, it was, the low point was higher, and the high point also lower. With the new Grouse Bike Park under construction, I’d have to turn back at the property boundary, the classic chairlift to chairlift Triple Crown wasn’t a possibility but I made it as far as possible. After an iconic Fromme descent, I entered the labyrinth of the British Properties, to me this was a true test of my preparation for the route. I managed to get through this maze without having to check for directions, that was some nice reassurance. One more mountain to go, Cypress was next on the menu. This climb is always a chore for me, by the time I came onto the road I had 600m of climbing and only 2 switchbacks, despite making steady progress it felt like I wasn’t moving.

As I approached the top the road flattened out giving me a rare opportunity to spin the legs out, increase the cadence and loosen up. An F1-style pitstop at the vending machine at the carpark was a crucial part of my plan and one of the things I’d been looking forward to. Next up was an arrey of classic north shore trails weaving through the Cypress forrest, this was the cherry on top and was an epic way to round out my first Triple Crown. A quick spin out on the highway and I’d arrive In Horseshoe Bay, 6 hours 35 minutes after starting. I was shocked by this time; I’d prepared myself to arrive at close to hour 10 and expected this whole challenge to take me upwards of 30 hours. My mind was conflicted, I didn’t know if I should’ve been feeling stoked that I’d be finishing ahead of schedule or concerned that I’d pushed too hard? A reset was needed. In my mind, this was the end of the ride, and I was simply going to head out for another. I changed into a fresh set of clothes, went through my pre-ride routine, chain lube, pressure check and sat down at the park bench and chomped my way through a large pizza. This stop set me back an hour, but I’d mentally prepared myself for being on the bike for 30 hours. I was far enough ahead that I decided spending an hour to set myself up for the last 2 Triple Crowns would do me much more good than harm.

- The Top of Cypress littered with road bikes...and some mountain bikes.

- Crucial fuel stop.

18:30 - 1 ⅔ Triple Crowns Completed

The small rest did me wonders, my body didn’t skip a beat with the back-to-back laps of Cypress, the thing I’d previously been most worried about. It was only once I was back on the slopes of Fromme did my body start to remind me that it had been a big day. From Horseshoe Bay to this point (Except the descent) everything had been a smooth, fast, paved road. Transitioning to the dampened gravel climb on Fromme I was painfully reminded of how my body was feeling. I was managing fine but there was some lingering discomfort that I could have done without. I kept chugging along knowing that it would only be so long until I was pointing down the hill on one of the most flowy North Shore descents. I arrived at the top, visibly fried, but internally the fire was still burning. Whenever I need a wakeup call, I like to throw myself down a trail faster than I should be going. For me, nothing tops the feeling of getting sketchy and having a truckload of adrenaline pumped into your bloodstream. Seventh Secret delivered the sketchy moments and Expresso brought the stoke. I was back in good spirits and was holding a good pace heading towards Seymour.

- Nose picking down shore trail? Heck yes.

21:30 - 2 Triple Crowns Completed

The traverse around the base of Mt Seymour was a tedious task, I chose to follow a mixture of trails, paths, and roads that required lots of turns and mental energy. It was well and truly dark as I began the climb up Seymour, my mind stayed alert, wondering if it was wind rustling leaves or bears wandering through the forest. The legs pushed a good pace up the hill, I was feeling confident I’d get this done. I rolled back into Deep Cove at 9:30 pm, completing the second Triple Crown in 8 hours from when I left Horseshoe Bay. I was still ahead of my predicted time, so I went for the same strategy of having a reset. I changed into a new set of clothes, cleaned myself up, ate a kebab and made sure my electronics were charged for the last stint. After another hour's break, I scraped myself up from the ground and was ready to get into it again.

Matthew wasn’t the only one tired after 2 Triple Crowns. Old, tired wood features sprinkle the dark corners of each of the mountains.

01:40 2 ⅓ Triple Crowns Completed

The legs took about 20 minutes to get into the flow of it, but from there I was having no trouble getting back to work. Seymour was long but despite a third lap of it, I wasn’t bored, this was a good sign of where my mind was at. I arrived at the top gate right as the groundskeeper was locking up for the night. We both were surprised by each other. I was quite keen to keep moving forward but he pulled me aside to ask what I was doing out at this time of night. He went from telling me how you've got to make the most of being young to then passing on his political view. I was barely cohesive enough to have a general conversation, let alone one about politics. I wished the guy the best and hastily fled. I was dreading this next descent; my hands had been annihilated from all the previous non-stop descents. Whilst I enjoy a lap of CBC I knew it wouldn’t be a good time in the state my body was in. By the time I made it to Cambodia, I was able to loosen my grip and find some flow within all the tech features the trail is known for.

04:00 2 ⅔ Triple Crowns Completed

Once again, the climb up Fromme was a good reality check of how I was feeling. My body was seemingly alright, I wasn't having any trouble keeping the legs spinning but it was evident I was beginning to hit a wall. My eyes were dreary, and I realised this would soon be a battle, I bumped up the power on the lights and pulled my phone out for a scroll session in hopes that a dopamine hit would pump some life into me. I arrived at the top relieved I’d made it, without too much of a struggle and I knew the next descent would wake me up. All was well and at this point, there was no way I wasn’t going to finish. Although it was evident It wouldn’t be a cruise to the end.

- Dark and Dank. Classic PNW.

07:40 3 Triple Crowns Completed - The Finish

I took a 45-minute break at the bottom of Mt Fromme, I needed a strong reset heading into this last climb, my legs weren’t a problem, but my body was starting to show signs of wanting to put itself to sleep. Most of the time I can push through physical discomfort, but as soon as my body decides it wants to go to bed that is typically the end of the line. I took a 45-minute break to fuel up, warm up and prepare myself for what could have been a very long climb up Cypress. I set off, riding over the dam and into the British Properties, for the first time I looked forward to this. My mind needed to be occupied and the labyrinth which was the neighbourhood made everything easier. As I made it onto the long straights of Cypress it began to hit me. I was struggling to stay awake; I was doing everything I could to distract myself, I’d begun riding faster hoping the physical effort would wake me up. I’d managed to hold myself together until I hit the flat section along the top, the drop in effort put me to sleep. My eyes closed themselves whilst riding along at about 18 kilometres per hour, as I began to crumple into my bike, I woke up with enough time to redirect myself into a ditch, away from the pavement. Thanks to a couple of new scrapes, I was feeling awake now, I didn’t have long until the descent, I knew if I could get that far, I’d make it to the finish. There was a huge sigh of relief as I approached the top, I was done, no more climbing. All downhill from here. That last lap down Cypress would have to be one of the loosest descents of my life, I hadn’t slowed down the pace, but I wasn’t all there mentally. I was bouncing my shoulders off trees left right and centre, but I held it together. From there it was only a short road ride out to Horseshoe Bay. I dipped my tyres in the water and that was it. I’d completed the Triple Triple Crown in 25 hours and 40 minutes. Overall, I’m stoked with the performance I gave that day, despite things falling apart right before the finish the ride I put together is something I won't be forgetting anytime soon.

The North Shore has a way of humbling even the most prepared riders, and my journey was no exception. The Triple Triple Crown pushed me to my physical and mental limits, forcing me to confront discomfort, fear, and fatigue. Each climb tested my endurance, each descent my skill and nerve. Yet, as gruelling as it was, the ride revealed something deeper. Profound respect for the land and the community that shaped it. The North Shore isn’t just a collection of trails, it's comparable to a living, breathing entity, rich with history and character. I now feel connected to the Shore in a way I hadn’t before, its ancient trees and rugged trails etched into my memory. It’s a place that doesn’t hand out victories easily, but when you leave its woods, battered and exhausted, you carry a piece of it with you. This ride taught me that to truly ride the Shore is to respect its challenge, embrace its beauty, and become part of its ever-evolving story.