Q & A with Annie Evans: Making of The Longest Night

In December of 2021, Annie Lloyd Evans became the first person to complete the Highland Trail 550 route in the winter. I followed along on Instagram at that time, but I didn’t truly appreciate how huge this challenge was until I watched her film, The Longest Night. Annie completed the route solo and filmed and produced The Longest Night with her partner Huw Oliver. The film shows the ups and downs and challenges of her dark, cold, and soggy winter ride as well as the beauty of the terrain of the Highland Trail 550 route. Annie was kind enough to answer our questions about her experience during her ride and about her filming. Give the film a watch and learn more about Annie and her ride in the interview below.


The Longest Night: A film by Annie Lloyd Evans and Huw Oliver

Could you give us a brief summary of your history with the Highland Trail 550 (and maybe some of the other highlights of your bikepacking life)?

I first heard about the Highland Trail 550 when one of my colleague’s partners, Iona, became the first woman to complete the route. That was back in 2014 and I thought it was a weird thing to do. I love technical riding and am drawn by fun singletrack. Riding that far, with so much double track seemed like an easy way to have a bad time. However, I did a lot of dirt road touring in places like Iceland and Patagonia over the next few years and found pedaling was acceptable if it took you to good places. Eventually, after having a go at races like the Arizona Trail Race and Colorado Trail Race, I thought I’d better give my local one a shot. I joined the group start in 2021 after the 2020 start was canceled.

What were your motivations for wanting to ride the Highland 550 in the winter? Why did you choose to document it in the manner you did?

I thought the HT550 would make a good fundraiser as a winter ride. It seemed to tick the boxes of long and miserable enough to get people willing to donate.

I struggle with winters in Scotland, they are long, dark and wet. With COVID restrictions preventing travel, having a challenge to work towards seemed the best way to keep my head happy. Initially I was going to do it in 2020, but we went back into lockdown before I had a chance. Alan, the route organizer, was very supportive and thought making a film would be a great idea. He is a big champion of getting more women into the group start and saw this as a way to inspire other women to sign up. He is hoping for a 50/50 split in 2023, so if you are reading this, consider signing up. 

I was always going to do the ride, but it seemed worth documenting even if that meant taking the “purity” out of the ITT (individual time trial). Although I’m not fussed about that anyway, I can’t imagine it’s high on many people’s list, so it’s a silly claim to have! Huw hired some long lenses and we borrowed a drone so he could film with as little impact as possible. I self filmed to try and give a real impression of what it was like.

Annie Evans. First finisher of a winter Highlands Trail 550. All photos courtesy of Annie Evans.
Riding during the longest nights.

How did preparations for this ride differ from when you raced it in the summer? 

My main worry in winter was the cold- getting soaked and not being able to warm back up. I carried a lot of extra kit compared to summer. I never weighed it, but I imagine I started with about four or five extra kilos. I was carrying dehydrated meals for eight days and a stove in addition to much warmer sleep kit and a huge high-altitude down jacket. Even on a normal day at work, it’s a running joke that I’m bundled up like it’s the Arctic. I hate being cold and struggle to re-warm. Getting too cold would be a big safety issue on the remote parts of the course with no phone signal. The extra weight was totally worth it and I’d carry it all again.

After completing the route in summer, I knew I could do the distance. So I was mostly going out on long rides in bad weather (one way to get excited about a weather warning) to test out kit and layering. I also wanted to try out different techniques for the hike-a-bikes. I’m not very strong and struggle to do a single pushup, so I find the steep, rocky pushes hard. I worked out that if I took my big Hyperlite Mountain Gear rucksac, I could take my bar and seat bag off the bike and carry them. It probably saved my ride as I don’t think I would have got through the deep wet snow drifts without that ability.

How does the experience of riding a route solo compare to being part of a grand depart for you?

I really enjoyed both the grand depart and the ITT. They were very different. The main difference was I felt much less pressure when riding solo. I do find dotwatching a bit odd when people start comparing riders and playing them against each other. One downside of the small women’s field is those pink dots really stand out, and although everyone is there with different motivations and preparation, it seems some dotwatchers assume you are racing to beat others, not finish the course as best you can. I didn’t like feeling I was being compared to other riders. As a non-competitive person, I cannot wait for women’s fields to get big enough that I can just cheer on the others from the back of the pack. But the big upside of the group start is the friendships and companionships that you can form. Also, when you hit a tough bit, or bad weather, it really helps knowing that other riders are experiencing the same things.

Tell us a little bit about Bike For Good, the charity you were raising money for? Why did you choose them?

Bike for Good is an amazing charity based in Glasgow. Their main aim is to get more people commuting by bike as a way to improve both mental and physical health, and also the health of our environment. They refurbish bikes and sell them at very affordable prices. They also run both cycling and mechanics workshops to build confidence and skills in the community. They do women and non-binary courses to try and increase participation in under-represented groups. I believe that cycling should be for everyone and I know just how much joy and health it brings me. I wanted to choose a charity that would help other people find their way into cycling. I’m so grateful to everyone who donated to them.

How often did you pull a camera out to film? Were there specific events or emotional states that you thought were important to document? Did filming ever feel like a burden? Were there any challenges filming in the cold weather? 

I got the camera out when I felt there was something worth filming, be that my emotions at the time, or something interesting with the scenery. There were times that I didn’t bother, as the weather was so bad I just wanted to keep moving. Actually, one of the biggest downsides of filming was I wasted a lot of energy worrying about Huw. I lost my dad very suddenly and since then, have a tendency to catastrophize things in my head. There were a few points where I was nearly having full-on panics imagining all sorts of horrible scenarios. I felt pretty safe as I had the tracker, but he didn’t. Although we hadn’t planned where he might film, with limited daylight I expected to see him in certain places. Sometimes he was just too sneaky and other times he was delayed by the snow conditions. It took a lot to rationalize my thoughts especially as I grew more tired.

For me, it would have been much easier to maintain a happy headspace without the filming. I found it disruptive whether I was self-filming or if Huw was around. Whilst he was mostly very discrete, there was one section coming into Ullapool, the first big town to get food for ages, where I had run out of food a couple hours ago and was hanging. Huw was really keen to get a specific drone shot so he wanted me to wait about till it got a little darker. All I wanted was the shop and several thousand calories. In the end, the drone clip didn’t even make it into the film. But I appreciate he had a very hard job and it was the only time it felt like he interfered with my ride.

Was it difficult to decide what footage was used and what was cut? How did you decide? Was there anything you filmed that when you got back you thought, “Oh, I don’t know if I want the world to see me in that state?”

We didn’t actually end up with that much footage. Because of the limited light, Huw was only in one location per day, so the opportunity to get lots of footage wasn’t really there. There was a bunch of stuff of me talking to my camera in the dark that didn’t make it. No one needed more of that in the film! I found it hard to film when I was very emotional and of course there are some bits I didn’t film. But I like films that show you the real experience, rather than the slick Instagram version. So although it was very hard to watch it back (and that was a big reason it took so long to make), it was something I felt was important. I do cringe when I look at some of it, but who cares how you look when you are out doing cool stuff?

Since you’d done the route before, did you have things or locations you planned to film, or did you just wing it while you were out there?

There were lots of places I would have liked footage, but we were so limited by the short days that it ended up being just whatever worked with where I was during those hours. I think Huw did a fantastic job of predicting where I would be and he had lots of early starts and long rides in to get to places to make it happen. When I was filming the woman’s field in the group start this year (watch this space for that), I got to indulge myself with 17 hours of daylight rather than darkness to capture their experiences. 

A lot of the drone footage Huw took was whilst he was waiting for me. It’s really funny, all those beautiful inversion clips, I never saw that at all. By the time I arrived, the mist had risen and swallowed up the trail. I was just inside this cold gray cloud. Huw did well to reassess his shots to account for the change in conditions by the time I arrived. But those drone clips were too good not to include. We want to inspire others to come and ride the route so it was nice to show the nice light.

How did filming and editing with just you and Huw compare with other media projects that you’ve been part of? What was it like to be fully in charge of so many aspects of this project, from riding to filming to editing? 

I’ve only been involved in one other media project, I did lots of self-filming that slowed me down loads and in the end none of it got used. Although I liked the film that was produced, it was interesting to see how it focussed on different things than what I would have chosen. It made me want to take control over my own narrative and tell stories how I see them. It was really special to create a whole film with just the two of us. It feels a lot more personal and I think the story telling benefited from that. It might not be as slick or polished as a professional team, but I’m proud of it.

How did you decide to do a longer length film than ones you’ve made in the past?

I make little YouTube videos and I kept getting feedback that people wanted slightly longer form content. So, I asked my Instagram followers how long they thought this film could be 🤣. The consensus was around half an hour, which was the length of my initial edit. But Huw has a much finer eye for detail and is more ruthless with editing, so he went through and streamlined it to make it all a bit flowier.

Do you have advice for other people planning an adventure who want to document it in a similar manner?

Just do it. It will feel faffy and stupid and you might think you aren’t capturing anything worthwhile, but it’s so much fun to see what you recorded and put it together. Take more batteries than you think. It’s always worth taking the time to put the tripod up. Your misery will be very funny/moving/motivating to someone else. Telling stories is powerful and film is a way to really share the experience.

Do you have plans to do another adventure ride or race soon? Can we expect to see more films from you in the future?

I’d love to keep making films, it’s really fun to learn and play with. I hope that one day I might be good enough that someone will let me make a film about them and I can stop having to watch myself 😂.

I’m hoping to make a group start or two next year, but after COVID and not leaving the UK for so long, I’m really looking forward to a long tour somewhere with big mountains and a new language to learn.

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