How to win the Highland Trail 550

The dust (or mud as is usually the case) might have settled on the 2022 edition of the Highland Trail 550 (HT550) But entries for the 2023 edition open on the 26th November this year and I’m sure there are many of you that have considered attempting one of The classic off-road ultra-endurance races in the world.

According to the HT550 website:

The Highland Trail is a self-supported mountain bike route 550 miles in length with over 16000m of climbing. It was inspired by events in the US like the Tour Divide and particularly the Colorado Trail Race (CTR). Initially put together as a simple training ride in preparation for the CTR, it became apparent that the great trails, beautiful scenery, remote wilderness, and fickle Scottish weather, offered a world class route for a self-supported challenge right here in UK. The majority of the route is on excellent trails and quiet roads, but includes some boggy and very technical sections. Everyone should expect some extended periods of hike-a-bike, even the best climbers and technical descenders will find plenty of terrain beyond their ability.

One person who know more about the race than most, being the first woman finisher in this year’s race is Tailfin R&D Division rider Gail Brown.

Before HT550 the folks at Tailfin asked ‘what advice would you give someone looking to finish Highland trail?’ I obviously didn’t feel qualified to answer that question, I wasn’t sure if I’d be finishing myself. It isn’t just me being modest either, the route is unforgiving, technical and remote. 550 miles of pedalling the most glorious bits of Scotland; wading through rivers, lowering down 2m peat cliffs into thigh deep bog, hiking up rocky scrambles, descending jagged, loose footpaths with views that take your breath away. Alan Goldsmith has created something that is far beyond a bike ride, something that it would never be a guarantee to get round. 

Now I feel a little more able to share my experience but I appreciate that completing the route once doesn’t qualify you to do so again. To a certain extent being a rookie was useful, blissfully unaware of the difficulties to come and with the sole goal of finishing. Perhaps this was the easiest version of HT550. But there are certainly some things I was glad to have learnt and would take forwards should I ever try again. 


I was feeling somewhat optimistic about the weather, it didn’t look like it would be too wet or too cold but if I know anything about mountains it’s that you should go prepared. As I was cycling into the darkening gloom on day 3 having trudged the Ledmore traverse, I was thankful to have taken this approach. The rain was properly set in, drops were coming down so heavily it felt like there was more water than air in the sky. I was looking for somewhere to sleep, the tree line that had looked so appealing on the map was dense and dripping. The likelihood of me getting my tent up without everything getting hideously damp seemed minimal. I cycled on, hoping to see some shelter soon.

On the side of the road I spotted a little shed, ever hopeful, I peered in. On one side there were bins filled with cardboard, on the other, enough space for me and my bike. It was going to be the driest place for miles. I peeled off my waterproofs and thanked my past self for bringing decent ones, I was pretty much dry underneath despite getting an absolute soaking. Setting up my bed I used cardboard for extra insulation and shivered my way through the night, it was genuinely colder than I’d expected. I’m very aware that compared to previous years, the race was blessed with ‘good’ conditions. If you’re contemplating HT550, come prepared for some serious mountain weather, no matter the forecast. 


Fuelling is up there with the most important part of any ultra distance sport. If doesn’t matter how fit you are, if you’re not good at eating, you’ll have a miserable time. One of the fabulous things about my Tailfin set up was that allowed plentiful storage for real food. Having a dense mix of macronutrients always helps me stay strong till the end. I steer away from simple sugars, they tend to give me mouth ulcers and last as long as putting matches on a fire.

I was able to take higher volume for the road, it wasn’t unusual to have my bags filled with several different pies and sandwiches, spanish tortilla, boiled eggs or something refreshing like sweet peppers. However, my favourite resupply, that managed to last me from Dornie until Fort William, was a trip to Manuela’s Wee Bakery. Honestly, it looked like the fairytale house made to tempt in Hansel and Gretel, or more worryingly, a hungry bikepacker. I bought breads covered in cheese and dripping with oily sun-dried tomatoes and olives, mini pizzas and flapjacks but the thing that got me up in the morning ready for my assault of the Pylon Climb was a ginormous croissant filled (and that is not an exaggeration, it was actually filled to the crust) with Nutella. I would definitely recommend taking a set up that allows space for food. 

Technical Ability

HT550 wasn’t on my radar last year largely due to it sounding too much like a mountain bike race. I’ve been riding a hardtail for just over 2 years and although I’m getting more confident on the trails, I can’t take on large drops, gaps or hop obstacles. I’d seen pictures of people descending the Devil’s staircase and plowing through rivers and heard people say that you needed to be able to jump waterbars to be able to do HT550. So I was pretty concerned I was going to end up with a mechanical or off my bike pretty quickly. As a result I was cautious, getting off and walking when I wasn’t sure whether I could ride. Interestingly what I found was that this didn’t slow me down as much as I’d thought.

Walking was often more graceful, I could retain flow and conserve energy, my risk of injury and mechanical was much lower. I do think I improved technically during the race and by the end I knew what waterbars I could roll and which ones I had to get off for. But my lesson is, this race is possible with basic off-road ability, as long as you know how to look after yourself in the mountains, you’ll be fine. I’d love to race again with better skills, but even then I would practice hike-a-biking, there are plenty of un-ridable sections whatever level of rider you are. 


It was really interesting comparing my experience to other competitors, it seemed that a lot of people were already deeply connected to the landscape, they knew the place names and the shape of the mountains. A lot of people had planned where they would like to get to each day and where their ideal resupplies were. I was coming at this with little or no expectation, with an idea of resupply opening times but no plan, and I can’t help but think that was an advantage. For me, the route was non-stop discovery. I think the best mindset for me during these events is one of exploration, no matter what the situation I’m curious how I’ll react. This often means that the harder it gets the happier and more motivated I am. It’s a choice after all, the ultimate privilege, to choose your own challenges. In whatever form I did the race next I’d try to take the same curious mindset rather than a fixed one. 

So in summary, what advice would I give; technique isn’t everything, practice walking, get out there, take some good waterproofs, eat all the food and explore what you’re capable of. Oh and don’t forget your chain lube…although if you do (like I did), turns out olive oil works pretty well!