The Longest Night – A Winter Ride on the Highland Trail 550 (Video)

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“The Longest Night” is a new 23-minute film that documents Annie Le’s incredible ride of Scotland’s Highland Trail 550 last December. Find out what it’s like to ride one of the world’s most challenging trails in the dark and cold of winter here, along with some background on Annie’s trip and a detailed packing list…

In December 2021, Annie Lloyd Evans (@a_girl_outside) attempted to ride the infamous Highland Trail 550 route in Scotland, having already been the fastest female finisher in that year’s May group start. If successful, she’d be the first person to complete the route’s 550 rugged miles in winter. More importantly, she was fundraising for the Glasgow-based charity Bike For Good. Having chosen to attempt the route over the shortest days of the year, the sun didn’t rise until nearly 9 a.m., and it set again by 3:30 p.m., offering just seven hours of daylight and long, dark nights to contend with.

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

This film, The Longest Night, charts that journey through a mixture of self-filmed footage and additional material from Huw Oliver. While not a fully self-supported ride in the strictest sense, this approach was okayed beforehand by the route’s creator, Alan Goldsmith, due to the uniqueness of a winter attempt and the opportunity for spinning a good yarn to pass those long winter evenings.

“I had so many moments of self-doubt, feeling stupid for trying, and thinking I would never finish. I discovered fears I never knew I had, and the long hours of darkness made it so much harder. But I also spent most of the time grateful to be out, happy to ride my bike and enjoying problem-solving my way through the difficulties.”

Scottish winter weather is famously unpredictable, and deep snow on one of the higher passes nearly ended Annie’s attempt early. She persevered through the drifts and stormy weather, though, with only a few tears along the way. On the fifth morning, a period of long-awaited calm allowed the mountains of the far northern highlands to glow with a stark, wintry beauty, and in the space of five minutes, all that horrible weather could be forgiven. Like any bikepacking avdenture, the challenges of a ride like this one forced her to examine her motivations and find contentment from within. She knew the mountains don’t care and wouldn’t change for her, but she could choose to see them in a positive light.

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

Highland Trail 550 Winter Gear

Scotland’s famously wet and windy winter weather presented some unique challenges as Annie planned which pieces of gear would be best suited to help her take on the Highland Trail 550. It required a lot more gear than a summer ride, so Annie prioritised comfort and the ability to change out layers as needed. Below is a summary of the gear she used:

Bike: Salsa Spearfish with Hope Tech 3 X2 brakes and Hope Pro4 hubs laced to ZTR Flow Mk3 rims with Teravail Ehline 29×2.5 tyres.

Bike bags: Revelate Designs custom frame bag, Terrapin 8l seat bag, Harness system with Salty Roll 15l dry bag and Egress front pocket. Mag-tank 2000 and Jerry Can top tube bags, and two Mountain Feed bags.

Clothing: 7Mesh Skypilot jacket and Revo Gore-Tex shorts. 7Mesh Gryphon baselayer and Hollyburn tights. She used Hope’s F20 flat pedals and wore Endura MTB overshoes over her regular riding shoes, as well as knee-length Sealskinz socks that overlapped so much with her wateproof 3/4 shorts that no water was able to get over the top and get her liner socks wet!

Revelate Salty Roll: All of her sleep kit apart from the tent… a Rab Neutrino 500 sleeping bag, Therm-a-Rest Neo-Air X-Therm mat, puffy jacket #1 (#2 was in her rucksack) fleece tights, fleece top, and puffy vest.

Egress pocket: This contained things she’d need during the day, e.g. spare gloves, a neck-warmer, 7Mesh Skypilot waterproof jacket, a GoPro, and lots of bulkier food items such as muffins, cake, donuts. Basically, it was a delicious bakery compartment.

Annie Le

Mag-tank 2000: Snacks.

Feed bags: A water bottle in one, electronics in a dry bag in the other (spare lights, headtorch, powerbank, charging cables).

Gas tank: Small items she needed frequently such as chain lube and a small rag. Multi-tool, suncream, moisturiser, butt cream.

Frame bag: She had lots of heavy items that didn’t need to stay dry inside, including a pump, tools and spares, a gas canister, food, tent pegs, and a poop trowel.

Seat bag: This had her Hyperlite Dirigo tent and ground sheet inside, as well as dehydrated meals and a whole lot of tailwind sachets jammed in the bottom.

Hyperlite Porter rucksack: Waterproof trousers, stove, and huge down jacket went in it, and it was also used for food when she’d re-stocked for a long stretch and needed the additional capacity.

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