The Long Night: A Winter Ride on the Highland Trail 550

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Back in December, Annie Le became the first person to complete Scotland’s Highland Trail 550 route in winter. Find a detailed retelling of her seven-day adventure through the Highlands, battling miles of snow, waist-deep river crossings, and dark days here, plus an extensive gallery of photos from Huw Oliver…

Words by Annie Le, photos by Huw Oliver

Snow tumbles around me as I stand and stare at the steep, snow-covered slope ahead. The hills are wearing zebra stripes of white against dark heather in the midst of the thaw, and the stripes of snow grow and merge as I climb higher. I’ve been pushing and dragging my bike through deep drifts for the last couple of hours, and the wet, heavy snow is almost impossible to force my bike through.

  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter

When crossing snow bridges over streams, I’ve been falling up to my waist, requiring careful decision making as to which sections are strong enough to support my weight. Darkness isn’t far away now, and I have another kilometre to go before I reach the top of the pass at Bealach Dubh. Earlier, I strapped my bags onto my rucksack to lighten my bike. Now, I’m going to have to carry my bike too if I’m to reach the top and be able to continue this journey. Only 70 miles in and I’m already crying, feeling utterly gubbed. How on earth will I be able to ride for another 500?

Step. Breathe. Step, then breathe. Slowly, slowly. Small steps.

As I inch my way upwards, I try to fight a rising panic and fear that I’m going to fail. After only 10 hours, I’m going to have to quit. I’ve misjudged the route and my ability. I feel stupid. I fall up to my waist yet again and fight the tears as I attempt to crawl out with my bike still on my shoulders. This is taking all the strength and energy I possess, but I’m still only moving at less than one kilometre per hour.

Annie Le, Highland Trail 550 Winter

Tyndrum — 0 km

I left Tyndrum in the Southwest Highlands at 6 a.m., feeling nervous but in high spirits. It was the start of my attempt to ride the infamous Highland Trail 550 route in winter, partly as a fundraiser for the Scottish cycling charity Bike for Good and partly as a personal challenge. I knew that I was going to experience the best and worst of Scottish winter: snow, rain, ice, big rivers, and 17 hours of darkness each day filled me with both dread and joy.

The route starts with eight river crossings in the first 20 miles. When I rode this way in summer, they were knee deep at most. In the dark, it was hard to judge their depth, and more than once I plunged in up to mid-thigh—so much for keeping my feet dry. Gale force winds alternately sped me forward and swiped at me from the side, like a cat playing with a mouse. A horrible screeching noise in the darkness to my right scared me until my light caught an old sheep pen, its tin roof lifting and grating in the wind.

  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter

As the light seeped into my greyscale world, I relaxed and settled into my rhythm. I had been making great time until the first snowdrift, just after Ben Alder Cottage. Some three miles of pushing later, I staggered over the bealach (pass) and dumped my bike on the snow. At least the pushing would be downhill from here. It was faster with lights switched on in the darkness, but disheartening to be pushing down the normally amazing singletrack. The moon popped out from behind the mountains and clouds, casting everything in a beautiful, glittering light. After remounting my bike and speeding down to Laggan, I considered my options.

I had the biggest pass of the route still to come, the Corrieyairack. It’s notorious for holding snow on its steep zig-zagging track. I knew the weather was set to deteriorate fast the following day, with intense winds on the mountains and torrential rain, and I had no desire to be up high in such conditions. Right now, I was completely exhausted, and there was no way I could carry and push through more miles of snow without a rest. I wasn’t even sure if I had the strength to make it over the pass at all. I stopped at Melgarve, a building that used to be a bothy but is now locked due to antisocial behaviour from visitors. I used its walls as a shelter from the gusty wind and pitched the tent as close as I could, crawling into it just as the rain started.

Annie Le, Highland Trail 550 Winter

Corrieyairack Pass — 135 km

I woke a few hours later, before my alarm. Stress about the incoming weather motivated me to get back on my bike before 4 a.m. As I climbed, I decided I would give it my best shot. No one could argue if I bailed out now due to snow or unsafe weather. I could retreat back down and just ride home and hide in bed for the next month. After all, I would just be one more on the list of people who’ve failed on a winter attempt.

I had to push long before the steep zig-zags at the back of the coire (bowl), but having learned a lot from yesterday’s snow, I was more efficient, wasting less time before offloading my bags to make it a bit easier. The zig-zags are cut into the hillside, steep banks on either side of the track perfect for collecting the snow. I worked out that if I straight-lined up the hill, I could link heather patches and avoid the worst of the deep drifts. I moved about 20 steps before having to stop and catch my breath, exhausted again. Normally, it would take me less than three hours to be over the hill and be eating pastries in the next village.

  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter

After five hours, I finally pushed up the last steep section to the plateau at the summit. The snow here covered the entire hill. Mist whirled around me in the strengthening winds, sleet stung my face, and I relied on following the line on my GPS to move in the right direction. Drenched in sweat, I was cooling rapidly in the brutal wind. A small, locked hut before the top offered enough shelter for me to strip off my wet layers and pile all my clothes on. I wasn’t at the very top yet, but there would be no more shelter from the wind, and I vowed not to stop for anything so as not to be frozen by the windchill.

As I rounded the summit, the wind fought me for my bike, trying to drag it out of my hands, and I had to stop and brace against the wind. I was caught on a patch of ice when a huge gust swooped down and nearly blown over. I longed for dawn. I was feeling very vulnerable up on this wind-scoured hill, still blindly following the GPX line over endless snowpacks. Here, at least, the snow was frozen and held my weight.

Annie Le, Highland Trail 550 Winter

Arriving in Fort Augustus felt like surviving some huge battle. It was 9 a.m. I’d started just over 24 hours ago and had spent 10 of those dragging or carrying my bike through the snow. I was completely and utterly done in. I was ready to lie down and sleep for days. Hot chocolate and a big bag of donuts from the shop helped my tired brain to form a plan. The weather was wild: heavy rain for the next 24 hours and strong winds.

I desperately wanted to be indoors, but the tourist-centric parts of the Highlands effectively shut down in winter. Cafés, shops, hotels, and B&Bs all take a much-needed rest after the busy summer. Finding anywhere became a tedious Google Maps exercise. I had done heaps of research for places further north, never imagining I’d need to stop indoors so early. After an hour of searching, I found an Airbnb that was open. It was only 10 miles further on, but it seemed to be the only option between my position and Lochinver, over 150 miles away.

  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter

Invermoriston — 163 km

At 2:30 the next morning, my alarm dragged me from sleep in the guesthouse’s big, cosy bed. Every inch of me wanted to ignore it and go back to sleep, but I got a chance to assess my body after dragging myself out. My neck and back were sore and stiff from carrying the bike, and my right calf had been cramping all night and felt useless. I forced myself to eat and think about the day ahead rather than the warm bed I was leaving. I was packed and ready to leave by 3:30, but when I opened the door to torrential rain, I thought better of it, retreating instead to lie down for another half hour.

By 5 a.m., I was nearly at the top of yet another big climb, bumping and weaving my way slowly along the shoreline of Loch Ma Stac, one of my favourite places on the trail. I couldn’t see anything in the murky gloom of the early morning and narrowly avoided riding into the loch on several occasions. Everything was soaked as I hit the road in the glen below, but the forecast was for the rain to clear, and the clouds finally thinned as dawn arrived.

Annie Le, Highland Trail 550 Winter

I was treated to a gorgeous sunrise as I crested the climb between Struy and Contin. Golden light filled the air and the world became beautiful again. I felt good. I had left my expectations behind on the dark snowdrifts of the Corrieyairack, and while I might have been slow, I was still out there, at least. I hadn’t quit, and right now that felt like winning. I stumbled around Contin Stores for a while, buying anything I thought I could convince my body to eat.

As darkness fell that afternoon, so did my mood. I’d been riding into a cold headwind as I made my way up from Croick towards Oykel Bridge. All my doubts piled back into my head. Why did I think I could do this? I was going too slowly. I was going to fail. I was so stupid for trying it at all. I’m usually good at staying positive, but I found it really hard to get my mind under control. I’d planned to camp near Oykel Bridge that night, but it sits in a low hollow where cold air gathers at night. I decided I would get a better night’s sleep further on, and so I dragged my negative thoughts onwards past Rosehall.

Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter

Bealach Horn — 395 km

Knowing more bad weather was on the way, another early start was in order the next day. I was at the bottom of the long climb towards the infamous Glen Golly and the Bealach Horn at first light. The rain had set in a few hours earlier, but so far the wind was holding off. I was enjoying the remote setting surrounded by rugged, craggy hills and fast-flowing streams. Waterfalls were rushing white and dancing down every hillside, like bigger versions of the rain running down my face and dripping off my nose. As I pushed up another set of steep switchbacks, the wind arrived in full force. Soon, I was not fighting the gradient as much as the roaring gusts that stopped me dead and had me leaning on my bike, fighting to keep any forward motion. This was far, far worse than the forecast I had seen while at Contin. It was meant to be windy, but this was something else.

Staggering slowly onwards, my progress dropped to a snail’s pace yet again. I had bought a bag of sweets specifically for this tough section, but even they weren’t going to be enough. A normally minor stream crossing was swollen and deep, and as I balanced precariously on some rocks, trying not to submerge my knee-high waterproof socks, my bike was pulled from me by the force of the water. Hanging onto one grip as it got submerged and pulled downstream, I leapt for the far bank. Feeling angry at myself, I dragged it out and checked for damage. Everything still seemed to be in place. My derailleur was unscathed. The dry bag on my bars had saved my sleeping bag from a watery doom. The sweets, ironically fish-shaped, were drenched and slippery, but delicious nonetheless.

Annie Le, Highland Trail 550 Winter

As I dropped down the huge peat hags towards An Dubh Loch, I watched waterfalls being whipped skywards back up their cliffs, and I realised that I was quite enjoying all the drama. There’s something about being out in a good storm that makes me feel alive. The rain battering my face was running inside my hood and dripping down my back, but I didn’t mind. I was warm and I was moving forwards, however slowly.

  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter

Changing from the “out” track on my GPX to the “back” track felt momentous. I was way behind my imagined schedule but excited for the miles ahead. The wind on the coast road pushed and shoved me, making me dismount for fear of being blown into the path of passing vehicles. I was going to miss the opening hours of Lochinver’s one small shop and eventually stopped for the night in a sheltered grassy hollow below the road, just short of town.

Lochinver — 460 km

The view down to Lochinver always fills me with delight. The wind had dropped when I arrived in the pre-dawn gloom, and the Christmas lights were dancing as they reflected on the still sea. I passed through the sleeping village, deciding to push on to Ullapool rather than wait for the shop to open. I was going to run out of food before then, but I need a night indoors to charge lights, and pushing on would maximise my indoor time. It was worth it too, as the most incredible sunrise ignited as I was halfway along the rugged push to Ledmore junction. The southern flanks of Suilven were caught in a dusky pink glow that intensified into deep purple and then shades of vermillion and orange over the next 40 minutes. Lochan Fada was a mirror for it all below me. I considered stripping for a quick dip, but couldn’t face the thought of pulling my clothes back on over wet skin.

Annie Le, Highland Trail 550 Winter

The trail, as always, took longer than I hoped, but this time because I chose to pause and look around as the light and colours changed on the surrounding hills. After the battering of the wind yesterday, the air felt at peace, gentle and encouraging in its stillness. Cam Loch could have been the most beautiful sight I’d ever seen on that brilliant morning. Not a single ripple interrupted its reflections, and I remembered to take a look back at Suilven, now dark under a cap of heavy clouds.

  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter

I arrived at Tesco in Ullapool just after dark. The track to get there had been surprisingly icy and incredibly wet. After buying round one of food, I ate as I phoned around guesthouses to find sanctuary for the night. My tired brain then tried to work out how many days until I was back in Fort Augustus, and I headed back into the shop to buy up the entire pastry aisle.

Annie Le, Highland Trail 550 Winter

Fisherfield — 600 km

Dawn saw me somewhere in Fisherfield the next morning. There wasn’t much difference between night and day—everything was shrouded in thick fog. With cold mist above and ice-covered trails below, the hills were invisible, and it was with relief that I found the river crossing at Shenavall only bum-deep (rather than boob-deep as it was last time I crossed). On the plateau leading to Carnmore I saw the sun indirectly—the brief sight of a fogbow over my head, but no more. The murk returned, closely followed by dusk.

The dark hours began to feel harder and harder. I’d planned my ride to coincide with the full moon, and imagining sparkly frosts, silhouetted hills, and beautiful reflections on the lochs, I’d been excited for the night. However, the moon mostly remained tucked up behind thick clouds or fog. I was riding in about 10 hours of darkness each day, and although I tried to split those hours into a morning and evening shift, I found a ball of dread in my stomach each time the light faded from the sky. Every part of me wanted to fight it, shouting that it was bedtime and wanting to be tucked up somewhere warm. I no longer wanted to be riding on empty trails, following a tiny dot of light as the mist blurred everything at the edges. The fog was an almost constant night-time companion in the second half, sometimes wet and heavy, sometimes freezing and causing my gears to stop working and my spokes to twang and ping.

Annie Le, Highland Trail 550 Winter

Another dusk, but this one would be the last. In Kinlochleven, I was stuffing my face with cake from the Co-op when I put my lights on one final time. A towering stag stood in the middle of the street as I left town towards the Devil’s Staircase and distant Glencoe. A freezing wind accompanied me, and I stopped to layer up, feeling intimidated once more by the high section I was approaching. “Focus on eating and moving,” I told myself, trusting that the simple rhythm of long-distance riding would see me through.

The Devil’s Staircase — 890 km

I got a fright as a walker emerged out of the mist. He had no light at all and was stumbling on the ice. He grunted hello but didn’t stop, marching on past me. Fifteen minutes later, after I’d fallen on the ice, I realised he was back. This time he stopped to chat, and it turned out he was descending the wrong side of the hill, having gotten confused in the mist. After refusing several times, he finally accepted my headtorch and was off again in the right direction this time, swallowed up into the mist within metres.

I took a short pause at the summit. I had imagined being here on a beautiful sparkly moonlit night, looking out over the moor to the looming silhouette of Buachaille Etive Mor. Instead, my vision was reduced to a couple of metres. Between the ice, fog, and my ever-growing fatigue, I simply couldn’t ride the loose and rocky descent safely, and to crash out now would be painful in more ways than one. There were about four hours left in this journey of mine, and as long as I didn’t mess up, I thought I might actually finish. The cobbled track over Rannoch Moor passed in a monotonous grey-cold blur. When I reached this point on my summer ride, I was in so much pain that the vibrations from the rocks were almost unbearable for my swollen feet. This time round, I was incredibly grateful that they were merely uncomfortable.

  • Annie Le, Highland Trail 550 Winter
  • Annie Le, Highland Trail 550 Winter

As I closed in on the finish line, I thought back to that first day spent stumbling in snowdrifts, convinced I wouldn’t complete the route at all. I thought of how I felt like a failure checking into a guesthouse on only my second night. Picturing the challenge as a whole had been overwhelming, so I had focused on waking up every day and trying to do my best, whatever that looked like.

Slowly, the miles had ticked by: some easily and joyfully, others hard-fought. The darkness and the trail conditions had made this ride considerably more challenging than I’d expected, but the ever-changing winter weather had also made it interesting and extremely satisfying. Scottish winter is notoriously fickle, and I got to see the best and worst of it throughout my week on the trail. I had seen everything from the gales and torrential rain early on, to fighting over the Bealach Horn amidst roaring waterfalls, to misty morning inversions and brittle sunlight, everything rimed in ice and the air still and crisp. During a normal week, I would have missed all of it.

Annie Le, Highland Trail 550 Winter

Tyndrum — 900km

After an age, I dismounted at the stile under the railway—one final obstacle to manhandle the laden bike over. It took about 10 minutes as I slipped around on the crumbling old stile, nearly dropping my bike several times before I finally made it over. The finish came 15 minutes later, where Huw and his mum stood waiting in the lonely pools of light beneath the streetlights. I arrived back at the same Christmas tree, its lights still bobbing in the wind, that Huw had photographed me beside before I set off seven days and sixteen hours earlier. To mark the occasion, Huw snapped the same photo of me again, looking very much the same as I did a week earlier. There are bags under my eyes where there were none before, and also a little glow of pride that wasn’t there either.

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