Unravelling: A 2022 Highland Trail 550 Story

Words by Huw Oliver (@topofests), photos by Annie Le (@a_girl_outside)

I lie in my bivvy bag in the bark chips beneath the kids’ playground, and in the small gap between stopping and falling asleep, I think to myself that perhaps I’m nearly there. The place I’m trying to get to is unclear, and I’m still unsure of the directions. The harder you try to look for it, the more elusive it becomes. But, once visited, you’ll want desperately to go back—though the price of entry is high. If you’ve ever ridden as far as you thought you could, and then further and a little further again, then you probably know the place.

Every year is drastically different on the Highland Trail, thanks to a combination of wilfully spiteful Scottish weather, the whims of organiser Alan Goldsmith, and all those small but decisive factors that determine your fate between starting and arriving back at the same point some 550 miles later. The last two times I started, in 2018 and 2021, ended unpleasantly: heat stroke, an ambulance, exhaustion, shingles. Disappointment, self-doubt, and a need to prove to myself that I can still do this have festered ever since.

I don’t have much gear strapped to my bike, but it feels like the weight of those past experiences has found its way into my bags, as much as I try not to let them come along. I don’t feel pressure to perform for other people, but I’m anxiously waiting to find out if I can live up to the past version of myself who has ridden so far and so fast before. Do I really have the ability to do that when last year I could barely ride 10 metres without a rest after just 24 hours? The rational bit of my brain knows I was ill, but the other part still feels the nasty surprise of being completely betrayed by my own body.

• 
• 

The ride starts in the usual way at 8.30 a.m. on a bright morning: a lot of excited people ride off at a pace they can’t possibly sustain over 550 miles. I don’t find the “racing” aspect of it all that attractive, and I look forward to the point when we’re all just riding our own rides. I tell myself just to let them go, but I can feel every passing rider tugging on my ego and whispering that I could catch them if I just pedalled a little harder.

Plenty of people say they don’t like this first day with all its jostling and pressure. Usually, I would agree, but one of the best pieces of advice I heard this year was to concentrate on what is good about the first day instead. I’ve been lumping the highs of setting out—brief chats with friendly riders, the Ben Alder singletrack, familiar places—with the downsides. So, I start reframing things through a more positive lens, determined to do this with an attitude I can reflect on and be proud of.

I fall in with Rick, who has also noticed the number of riders passing us with ragged breath as if this is a three-hour blast. We chat, deliberately slowing things down, and at one point, Angus and Simon pass us beside Loch Lyon, explaining that they both went the wrong way around the loch for a few kilometres. No sooner have they said that than they’re gone, hunting down the riders in front.

Among HT550 veterans, there’s a saying that the first 93 miles to Fort Augustus are the warm-up. They’re relatively fast and easy, and the wise keep plenty of matches in hand to burn later when they’ll be most needed. I ride on my own for most of the day, with Rick and other riders always in sight just ahead or behind. On the Lairig Ghallabhaich climb, I see Angus again while he replaces a bent mech hanger, and somewhere in Rannoch Forest, he easily breezes past me a second time.

• 
• 
• 

I find Rick again as I leave Fort Augustus. We ride north together into the warm glow of the evening and chat about anything and everything in the way you do; the shared anxiety and excitement of adventure is the fastest way I know to break down the barriers between strangers. A couple of dotwatchers punctuate the easy rhythm, but otherwise, we both seem intent on enjoying the 60 miles to Contin, even as we ride into mist and drizzle on the infamous “Track of 1,000 Puddles.”

It’s around 12.30 a.m. when we reach Contin, and Rick says he wants a good sleep and coffee in the morning, so he’s going to wait for the shop to open at 6 a.m. I wish him luck as we separate, and I remember something he shared earlier: “When I feel low, I picture the faces of people I love, who make me happy. It works, man. It really does!” It sounds like the right approach, so I store it away for later—an extra ace up my sleeve.

I’ve been scavenging like this for months, spotting attitudes and values in other people I look up to, trying to incorporate them into my headspace, knowing the physical effort will take care of itself, and upstairs is where the real work happens. Shortly afterwards, I’m lying in the playpark, still waiting for the real ride to begin and feeling like it might be just on the other side of the two-hour timer I’ve set for a short rest.

• 
• 

The following day starts with a test I’ve been dreading for 12 months. Last year, the first day was uneventful, but the morning after, my body began a horrible process of shutting down and refusing to move as the fatigue-induced shingles infection made itself known. I limped and cried north ineffectively for another 10 hours before conceding defeat. I’ve done long rides since then, but no multi-day racing, so there’s a suspended moment while I begin pedalling and feel for energy that eventually seems to flow back into me, despite the miles and lack of sleep. I ease my way up Strath Vaich beneath a sun that offers illumination and renewal. I’ve passed this first test.

The long glens that morning aren’t my cup of tea. I’ve never been strong at long sections of flat pedalling, and the strengthening headwind slows my progress while delivering increasingly frequent showers. Today is all about the Bealach Horn, perhaps the most notorious section of the route, as well as its most northerly point. It’s where I scratched in 2018 after a stomach bug I likely picked up back in Tyndrum laid me out beside the trail. I was throwing up uncontrollably until dehydration and heat stroke made things even more serious.

It was my good friend and fellow racer Scott who abandoned his own ride to help me off the hill and into an ambulance, although I don’t remember much until getting to the hospital in the middle of the night. In a word, it was unpleasant, and since then, I’ve attached a kind of shame to the whole thing. Something about being incapable and vulnerable in a place where I’m normally comfortable and competent.

The approach to the bealach (pass) is intimidatingly physical and seems to attract bad weather like a lightning rod. The sections of trail are steep and rough, and one descent has little trail at all: riders pick their way down through tiers of peat bog that’s falling towards the glen below. It has a kind of intrinsic character, both beautiful and uncaring, and it’s impossible not to feel it when the looming walls of the coire make the solo element of this race very real. I sense it waiting for me up there in the north, so as I ride to meet it, I take Rick’s advice and picture the faces of the people who make me happy. I keep those faces close as I tread softly through the peat hags and puddles.

• 
• 

I slide my eyes away from the spot in the grass, just below the high point, where I curled up miserably in 2018, flying down the descent faster than I would normally dare, putting distance between myself and the past. Even the weather seems to be offering a little leeway as the showers ease as I approach Kylesku and its gracefully curved bridge. The next section is a long stretch of singletrack road that catches the unwary since it packs nearly 1,000 metres of punchy climbing into just over 20 miles. I was looking forward to it.

In 2017, I rode this section with Javi the Spanish singlespeed wizard. We watched the sun slide into the golden water of the Minch and pedalled with legs that could have gone on forever. It was one of the most euphoric experiences I’ve ever shared with anyone, and since then, I haven’t been afraid of this road. Tonight too, the coast road numbs my pain by providing sea views and the jagged troll’s teeth outlines of the Assynt hills.

I stop in at Drumbeg Stores, where the owners are avid dotwatchers who take far too good care of racers as they pass by in need of food and a friendly face. With veins full of coffee and bags repacked with food, I tell myself that I will make Ledmore Junction by sunset, ticking off a second infamously physical section of bog-trotting before the day is done. I learn at Drumbeg that only Angus is ahead of me, which is what I thought, and that he was nearing Ledmore while I was lounging at the shop, putting him some five hours ahead.

• 
• 

I’m a little behind Neil’s 2017 record pace, but Angus is flying into exciting new territory ahead of Neil’s virtual dot. While I spin out the final bit of trail into Lochinver, I wonder if he can keep it up over the much more technical terrain of the west coast. We’ve finally arrived at the section where I can travel lightly and draw the most energy from the landscape. Suileag Bothy passes by on my left at 9:30 p.m., the furthest I’ve ever reached on the second day, which brings the feeling that this is going to be a good night.

Treading lightly is the trick to the pathless, rocky, and boggy ground that makes the HT550 so charming. It doesn’t matter if you’re riding or walking, as long as you’re moving forwards with minimal effort, ghost-like. It’s just after midnight when I reach Oykel Bridge, closing the route’s northern loop and hitting an enormous personal checkpoint—not many people have done this before. The track is wet from the day’s rain as I head west towards Ullapool. In the face of mounting sleepiness, I put in headphones to listen to the Gaelic-electronic bagpipe fusion of Niteworks, which feels appropriate, and aim for Knockdamph Bothy to sleep, deciding that a roof will help against the lingering showers.

It must have been too cosy on the wooden floor of the bothy since I wake four hours later and two hours after my phone buzzed its alarm. My ankles have stiffened up, and I can feel the beginnings of tendonitis in my Achilles from the previous day’s hike-a-bike. In the chilly mist that guards the descent to Ullapool, my woolly brain wonders if there’s a way to avoid the whole getting-up torture altogether. In 2017, I rode from Torridon to Tyndrum non-stop. Last year, my partner Annie rode even further: Poolewe to home without stopping. I contemplate going one better and doing the 230 miles from Knockdamph to Tyndrum in one shot, neatly solving the issue of groggy morning sadness. It’s the sort of thing that makes sense just now.

Thoughts of tonight can wait, anyway, because Ullapool marks the entrance to the Fisherfield section and the crux of this whole thing. It demands attention and focus over the next 40 miles of rough trail and sternly beautiful mountains. It was 8:30 a.m. as I began the tortuously steep march up the “Coffin Road” to Dundonnell, and I lean into it even as my Achilles protest. The long, flat glens of the east require restraint and the ability to entertain yourself, but here in the west, the terrain leads the dance. You can try to impose your own rhythm on it, but it won’t work. Instead, I revel in the hard miles and slip into the rhythm of the place. Until last night, I’d been wary of distance and fearful of the cost of effort, but here I feel at home, and my legs know exactly what to do.

• 
• 

The river crossing at Shenavall is peat-stained and deep thanks to yesterday’s rain and the north-westerlies that pile up water at the eastern end of the loch. In no mood to waste time probing the changeable shingle banks, I head straight for the bar at the river mouth since it’s reliable, if a little deeper. The water comes up to my neck, but the weight of the bike above my head keeps me planted on the gravel even as waves lap my chin. The small but crucial decisions—deciding not to undress for the crossing, monitoring energy, warmth, and mood —are taking care of themselves in the background, with the collective goal of endless forward motion.

It’s milder today, and by the time I crest the hike onto the plateau, the loch water has dried from my clothes. It’s well over 24 hours since I’ve seen another rider. I know they’re out there too, but it feels, more than ever, like this is about me and my own head. The miles-wide amphitheatre of Carnmore and Dubh Loch is as obvious a reminder as any that this place is far too big to push against.

The shop at Poolewe provides the food that will see me to Fort William, and I try to get my tracker to send a position as I sit on the grass armed with an ice cream. I’m enjoying the anonymity, to be honest, both online and to the people wondering what this smelly cyclist buying all the egg sandwiches is up to. I don’t look at the tracker during races as a rule, since the only reason to do so is to check in on the competition, and the day I start racing against people rather than the clock is the day I stop and do something else.

I decide to go into the night with an open mind. It’s late in the ride, and the time for rigid plans is over. After feeling close on the first night, I’ve arrived in that liminal place I think is the real destination in ultra-racing. My body is exhausted, but now there’s a degree of separation from that feeling, as if fatigue is subjective and optional. The anxiety I brought with me to Tyndrum seems to have fallen away unnoticed like a snack from an unzipped pocket. There’s just the tick-tick-tick rhythm of eating, drinking, and turning pedals. This is the addictive, immersive experience that has always drawn me back to this route, but the fact that I’m having conversations with the local sheep and singing loudly would make it hard to communicate that to an observer. At one point, I think I watch an eagle swoop close overhead before realising it’s still dark, and I should probably take some caffeine.

• 
• 

Somewhere in Glen Lichd, mid-karaoke and feeling the high from two egg sandwiches hurriedly eaten in Dornie, I notice that the distinctive tyre tracks that have been my only company for the last two days have gone. The advantage of being a tyre nerd is that you know who else has passed before you, but now it looks like my tracks are the only ones. The only explanation is that Angus must have stopped to sleep somewhere out of sight. I feel the draw to ride harder, to “race,” but it only lasts a moment. What am I doing at 3 a.m. if not getting to Tyndrum as fast as my body can go?

Partway up the hike-a-bike, with waterfalls reflecting the first gloomy light of dawn, I catch sight of a bright light threading its way through the glen behind me; there’s only one person who that can belong to. It’s another 18 hours at least to Tyndrum, and I really don’t have the energy to be thinking about it, so I bow my head to the handlebars, tell my ankles to be quiet, and round the corner to Glen Affric, slipping out of sight.

Camban Bothy was my planned stop for the night, but it’s getting light, and I don’t feel the claws of the sleep monster, so with a quick hello to the figure beside his tent outside, I roll straight through. It’s 24 hours since I set off from Knockdamph, and it looks like I’m heading home in one shift. The excitement of going into the unknown territory of such a long stint adds a lightness to my legs as the sun begins its leisurely rise over the mist-cloaked and wooded shores of Loch Affric.

The Great Glen Way section is a relatively flat 34 miles down the immense fault line that links Inverness and Fort William. It’s a favourite spot for fatigue and doubts to get the jump on you, creeping into a mind without distractions. That’s been true in the past, but today I’m holding out—this is becoming less of a bike ride and more of a balancing act between movement and total collapse, and the line is getting thinner. I bump into Pete, who’s riding part of the route to catch brief audio interviews with riders as he meets them. At a point when our community is debating the balance between authentic storytelling and respecting the self-sufficient ethos of ultra-distance racing, it feels like a wonderfully raw and unobtrusive way to communicate what this means to us all, even if making full sentences is feeling harder than usual.

• 
• 

Pete drops the big one, “Why are you here?” and I’m not sure I have an answer. Just being here at all is taking everything I have, so there’s no space left to think about why. Perhaps that’s the answer, though: I want to see who I am when I ride so far that time and normality become detached and when just being is taking everything I have to give. It’s almost too simple, but I think it might be the truth. It could be about growth, or it could be about shucking off grimy layers of insecurity and past failure. I chew it over after I leave Pete behind, thankful for the distraction on the flat miles of canal towpath.

Fort William isn’t exactly the beginning of the home stretch. It’s around 50 miles and plenty of climbing away from Tyndrum, but something tells me now is the time to let it all hang out. It’s 1 p.m., and as I join the West Highland Way southbound, I climb past a steady stream of hikers approaching the end of their adventures from Glasgow. We’re going in opposite directions with wildly different journeys behind us, but I recognise the same weary elation in their eyes that says they too feel alive this bright afternoon. They don’t know it, but they lift me out of the shadow of Ben Nevis’ crags as the trail twists and dives through the Lairig Mòr—the big pass—to Kinlochleven.

I know every rise and fall of the route between here and the finish, and after three days, it feels like my bike could ride it on its own; I’ve felt stronger by the hour, and now I know I’m flying. The “sting in the tail” singletrack climb from Victoria Bridge feels like the place to leave the pain of past rides behind, and I ride it on legs that scream they truly are empty this time. In case I wasn’t getting the message that this is supposed to be a moment of cathartic redemption, a deluge darkens the sky and drenches the closing miles from Bridge of Orchy, washing away tears and snot and failure.

Of course, this is a bikepacking race, and my tracker isn’t working, so the two figures in waterproofs standing at the finish are all I’m getting. Ewan and Ian offer me a cup of tea, dry clothes, and an understated, very British pat on the back. After 3 days, 11 hours, and 24 minutes, it all feels perfect.

The days that follow feel like one huge exhalation. For the last five years, I’ve anticipated this feeling almost as much as the ride itself, wanting to luxuriate in the satisfaction of not moving that only comes after days spent restlessly in motion. Other riders arrive, and there’s that magic bubble of camaraderie and unspoken understanding at the finish that I want to lounge in for as long as possible before the spell breaks. It’s a kind of emotional debrief: a chance to unpick the thing you’ve just done with some of the only people in the world who know exactly what you’re trying to say, despite the inadequacy of words.

• 
• 

As I listen to people tell their stories, I notice which details get the most prominence: some lead with the quantitative and adversarial—time taken, position, opponents beaten—and others with the qualitative—a sight seen, a moment shared, a feeling. They’ve all ridden the same route but on vastly different journeys with different lessons.

What have I learned? What have I lost? I ask myself again if I’ve left bits of me behind in some of the lonely glens or if I’ve picked up new bits to add to myself. At the very least, riding this route continues to shape how I navigate the highs and lows of life and how I perceive myself. There’s an expectation that such a long time spent riding alone should bring revelation, but I’ve found an unravelling instead. The trail took a great tangle of knotted thoughts and feelings from inside me and slowly spooled them back out into the places they came from, one mile at a time.

The best of me feels tied to the best of this land and its capacity to enrich.

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