Meet Devin Milsop.Hiking in Aialik Bay in Kenai Fjords National Park.Kayaking in Prince William Sound.

Not So Average Jane

The adventures of Devin Milsop

Big Sky locals might recognize Devin Milsop from the time when she worked at the front desk at Moonlight; as a concierge at the Summit or when she was assistant property manager for Big Sky Resort. I know her as a fun-loving, pigtail wearing, dancing-in-the-dugout catcher for the Cab Lizards, in the Big Sky Co-ed softball league. She’s a person who always has encouraging words for others – even members of the opposing teams.

Milsop grew up in Philadelphia and decided on a degree in recreation, parks and tourism. 

“I wanted the very opposite of what I knew, and that was guiding – wilderness. Growing up I hated the city. What’s the opposite of the city? The wilderness; a tent – not showering for two weeks,” she said. 

Her initiation into the wilderness life involved some harrowing experiences, beginning when while studying abroad in Patagonia. The program was four months in duration: two months learning backpacking and glacial travel and two months kayaking. Milsop was the 12thperson in line to cross a snow bridge over a crevasse when the walkway crumbled, plunging her into the gap. 

Fortunately, she was wearing a backpack weighing in at nearly 90 pounds – big enough to serve as a wedge. Milsop stayed that way – stuck in a crevasse for about half an hour, while her cohorts figured out a plan to safely get her out. 

“Finally, I was pulled out. We were still a two-hour trek from our tents. So, I had to continue over the same glacial fields for another two hours,” she said. 

The group found their way to a remote “compo of a gaucho” and were invited to stay in the farmer’s structure. Mice attacked their food supply in the night. They had to dispose of the bulk of their rations due to a specific Chilean version of the hantavirus: ingestion of tainted food could stop a person’s heart in two hours – and they were days away from medical care. All that remained for sustenance for the group of over a dozen people was powdered eggs and milk. 

The group hiked on. Rough terrain; high elevation; no trail and topo maps as guides. The calorie demand to keep their bodies moving was much higher than what they could take in. They were starving. 

“So, we find another gaucho. We literally paid this farmer $70 U.S. dollars and a hat for a lamb,” she said. The lamb was selected; the farmer prepared to slaughter the animal. Starvation of that nature makes a person think differently, Milsop explained. Under normal circumstances she would cry, but in this case, she found herself volunteering to help with the slaughter. 

Her near-death experiences did not deter her from the wilderness she had grown to love. She went to Alaska next and spent four summers and half a winter there.

Milsop started her first season in Valdez, Alaska as a sea kayaking intern – missing her college graduation so she could take the job. By the end of the summer she was a kayaking/glacier guide and would take clients out for anywhere from one to nine-day trips in weather of all kinds.

She survived treks with seven days of consistent snow, crazy wind, icebergs, and sea lions which like to tap the underside of kayaks, sometimes causing them to flip. An unfortunate seal-flip would have meant nearly immediate hypothermia in the frigid water.

The area also had the largest tide swing in the world: up to 36 feet. Such a range demanded guides be extremely calculated when selecting a camping spot. Milsop never awakened with her tent under water, but some other guides did – and it was a terrifying experience. 

Next stop in Milsop’s Alaskan career was Skwentna, a locale accessible only by float plane or dogsled. She was responsible for guiding backpacking trips deep into the wilderness as well as serving as a waitress, a housekeeper, chopping firewood for all the cabins, taking care of all 17 sled dogs and even helping build a cabin. Child labor laws would have come into play if she were a kid, she said. “I hated that place,” she said vehemently. 

Bears were everywhere in Skwentna. Her third night on the job, she heard the sled dogs in a tizzy. The following morning, she discovered one dog had been mauled. She had to do something that even the hardened men of the famous and fated Shackleton expedition found sickening. 

“I had to mercy kill him – I had to shoot the dog. It was horrific. It was my fourth day on the job,” she said. “I cried for three days.”

Milsop was guiding into highly remote areas – places so far removed from the human footprint that bears hadn’t learned an aversion to people and – in Milsop’s opinion – looked at her and her clients as potential food sources. This was particularly true on one expedition. Milsop was guiding a mother and her five daughters under the age of 15. Groups of four or more are supposed to be relatively safe from aggressive actions from a bear, but not in this case. 

“It stalked us for about two hours and I didn’t let them know,” she said. “I finally turned around and he was uncomfortably close, so I prepped everyone for an encounter. I had to arm a 12-year-old with bear spray.”

Milsop explained that she would be out front and would engage her bear spray and flare – which is exactly what she did. The bear didn’t turn until it was about nine feet away. Her satellite phone was meant for such encounters, so she immediately called for an evacuation. 

When the helicopter arrived, she realized there was a problem: that particular helicopter only sat six passengers and she made the seventh. Someone had to be left behind with the bear – effectively remaining as prey for a predator. She was given more bear spray and waited alone for over an hour. 

“It’s like the fight or flight mentality comes in. I’m more numb, and the bear is still around. I think my best option is to sit in the stream, so I sit in a stream for an hour with this bear watching me,” she said. “My [expletive] boss made me go out there to the same place the very next day to do the same job. That was the end of my guiding career.”

Still, Milsop craved the mountains and first came to Montana in 2013 with a group of friends for one last adventure before they got their “big kid jobs.” She never left. Now she works for Expedia as associate market manager for Montana. 

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