Ashley Hill: Meet Royalty, Float on Air, Repeat

Few bikepackers brave the Top of the World Highway – a patchy 60-mile stretch of road that skirts the mountain crests between the Alaskan and Yukon border – because it’s mostly unpaved and when the rains come, they come hard.

But in June 2017, a figure pushed her way up the highway’s cold wet hills, striving for the Yukon border and beyond. Riding like a wild child – hair muddied and whipping into the wind – she screamed “YOU’RE NOT GOING TO GET ME” into the storms.

That figure was Ashley Hill, a badass Californian on an adventure that she would never have dreamed of a decade ago. But now, dreaming of adventures (and making those dreams come true) is her thing.

A wild child born with a spin of the globe

Ashley grew up in Silicon Valley, California, as far away from the Yukon as you can imagine. She was a typical ‘California girl’, more into malls than sports. Looking back on those days, she can count the amount of times she set foot in the wilderness on a single hand. Her most striking memory, perhaps, was camping with a boyfriend in a national park, and even then she borrowed a sleeping bag. Before her first hike – the one that would define her – she’d never seen snow.

Curious to discover how Ashley transformed from California girl to badass world adventurer, I drop her a line on a crackly Google Hangout. She’s in a Brooklyn apartment, between adventures. She’s relaxed and laughs and leans forward when she talks.

“I knew zero about the outdoors growing up,” she tells me. “I worked with special needs children and youth from the age of 14 and volunteered at homeless shelters. That was my passion. And when I was a little older…my passion was probably drinking and dancing! Like, a lot of drinking!” she laughs, reassuring me she earned her trail nickname ‘Bloody Mary’ for darn good reasons.

But things changed quickly. She married young and divorced young. It was an event that led to her first ‘rebirth’, as she calls it.

“It was 2009. I kind of spun the globe and landed a finger on Colombia and bought a one-way ticket. I didn't speak a word of Spanish. I didn't know one person in the country and I decided I was going to live there – it was amazing! I ended up loving it so much that I enrolled in the university to extend my stay, because my six-month tourist visa was up and I wasn't ready to go home.”

And she would have found a way to stay even longer...if it wasn’t for a phone call that changed her life. Her mother was diagnosed with Glioblastoma Grade IV (terminal brain cancer) and given a few years to live. Ashley headed home.

"I kind of spun the globe and landed a finger on Colombia and bought a one-way ticket. I didn't speak a word of Spanish. I didn't know one person in the country and I decided I was going to live there - it was amazing!"

“You know, we weren't close growing up. My parents were divorced and I was closer with my father. But with her diagnosis I kind of realized the importance of life, and shortness of it all, and what we have. So she and I became incredibly close for the last three years of her life.  

“She lived a beautiful life, she was an artist and she found her passion and career late in life...and she found her love. She was married to a wonderful woman who loved her in her last few years of life. You know, her choice might have looked unconventional or different to other people, but when you find the right half it's unstoppable, it's a beautiful thing.”

Meet royalty, float on air – check

After her mother’s passing, Ashley searched for a way to grieve. And so began her second ‘rebirth’ (the one she calls her most profound). One day she decided to walk from Canada to Mexico. Alone and with no experience. It would be her first hike, and it would be the Pacific Crest Trail (fondly known to hikers as the PCT), a hazardous 2,650-mile trek through mountains, desert and snow.  

She quit her job, sold most of her possessions and began to frantically research her adventure, scrolling through forums and online guides, scratching together bits and pieces of knowledge for what lay ahead.

“I got really lucky because I knew nothing and I had no friends in the outdoor world, and every day I was just researching, for months, looking up the smallest things such as ‘What does cold or hot spots on a foot mean?’, ‘What is this ultralight stuff that they talk about in gear lists?’”

And by fate or serendipity, an ad appeared on her screen: an ultralight company was sponsoring five first-time hikers with gear and supplies and the deadline to apply was that very night.

“I had, like, two hours to write my story and apply...but I got it!”

That company was YAMA Mountain Gear, a small Virginia-based “one-man shop,” Ashley tells me.

“They helped me out with the best gear for long-distance hiking, so I started off better than most people – and with mentors too.”

In the months leading up to her departure, Ashley would correspond with some ‘hiking royalty’ via phone and email. One of them was Heather “Anish” Anderson, the fastest woman to hike the PCT (in 60 days); another was a man Ashley calls Remy.

“He was my biggest support. He met me two days before my hike and gave me a shakedown with all my gear. I thought it was lightweight at 14 pounds – he got me down to 10!”

But all of Heather’s and Remy’s mentoring couldn’t prepare Ashley for what was next – a landslide crossing, three days into her adventure.

“I’d never walked on the snow. And it was a sunny hard day and there was an avalanche the year before, so this part of the trail hadn't been maintained; it's just this landslide with snow over it. So I was crossing with my ice axe and my trekking poles – and I just fell. I did everything that I'd researched and read about, self arresting (an ice axe technique), and there was about two or three feet of snow to catch before it was maybe a 2000-foot drop...down to death.”

But Ashley found a way to hold on. To drag herself up. And push on. She made it to Mexico, after five hard months on the trail. She suffered from altitude sickness. Screamed that she couldn’t do it. And walked through exhaustion. But along the way, things clicked. She found herself, alone in the wilderness, at peace with herself, at times feeling like she was floating rather than walking, with a new mantra on her breath: “strength and courage”.

"So I was crossing with my ice axe and my trekking poles – and I just fell. I did everything that I'd researched and read about, self arresting (an ice axe technique), and there was about two or three feet of snow to catch before it was maybe a 2000-foot drop...down to death."

One night in the High Sierras, too tired to pitch shelter, she slept under the stars by a lake – it was so cold her pack froze over. But there, she realized the weight of what she was doing, why she was doing it, and that she was, in fact, a hiker.

Storms bring more than rain

Since then, Ashley hasn’t stopped. In three years, she’s toured Southeast Asia by motorcycle, trekked the Pacific Northwest Trail, New Zealand’s Te Araroa trail, Vermont's Long Trail and the Hayduke Trail; and traversed Iceland. All solo and unsupported. Most recently, she rode a bike 1500 miles from Alaska to the Yukon.

As we talk, she sits and crosses her legs. Shuffles a little. She seems restless sitting in her apartment now, talking about adventure. She hints at bigger plans but tells me she’s currently “on hold right now,” and then smiles.

“My partner came out to Alaska with me and we made a baby. I didn't realize that was why I was so exhausted on this bike ride for months!” she laughs. “So we're going to wait until our baby's old enough, and then we’re going to cycle around the world as a family.”

When did this idea to circumnavigate the world come to her? During a storm in Iceland, of course.

“The search and rescue team wouldn't let me go over this mountain pass because the weather was too extreme. So I got off the trail, caught the last ferry to Westman Islands and rented a tiny cabin. It looked like a giant wine barrel with a bed inside. The whole island was emptied from a massive storm. There I had this epiphany: I wanted to circumnavigate the earth. And I spent all night (I couldn't sleep) writing out the idea. I was like, ‘How am I going to make this work?’”

Ashley scribbled her plan into her journal. And when the storm subsided and her journal filled up, she tore those pages from it; she keeps them with her wherever she goes, as a reminder of the promise she made to herself.

Ashley figures she can complete it in three years on bike – hiking would take about nine in her rough calculations – combining hiking, photography, writing and non-profit work with a focus on global poverty as she goes.

Some naysayers might scoff at her plan, call it impossible – especially with a child in tow. But they don’t know Ashley Hill. She’ll do it – the only question is when.

And I for one will be cheering her on... And taking note of how the hell she pulls it off.

Follow Ashley's adventures here. 

Ashley Hill's 'Tried and True' Trail Essentials