For Jessie Herman-Haywood, snowboarding is more than a hobby — it’s a lifestyle. The Juneau-born Alutiiq artist and athlete has molded her life around her passion for the sport, chasing the flexibility and freedom needed to maximize her time spent sliding on snow. For Herman-Haywood, snowboarding culture was where she first experienced a sense of true belonging.
Herman-Haywood started skiing at the age of five, but switched to snowboarding at age 12. Though it took her a couple of years to get past the growing pains of a new sport, it wasn’t long before she was enamored with the culture of the snowboarding community. “At the time, snowboarding was so intertwined with counterculture,” she says. “I felt like I was a part of something immediately. I felt very included.”
As a teen growing up with a single dad, Herman-Haywood felt like a misfit at times, but all of that disappeared when she was snowboarding. “I really clung to it,” she explains. “You have the togetherness in snowboarding — I was hooked.”
It wasn’t long before Herman-Haywood made a name for herself in Juneau’s snow community, winning the first big air competition she entered at the age of fourteen. She took a job at a snowboard shop in Juneau as a young teen and earned opportunities to access the nearby mountains for helicopter-accessed snowboarding. She consumed snowboard media, pouring over magazines and watching snowboard films, daydreaming about her future in the sport.
After high school, she moved to Mammoth Lakes, California to pursue the art of riding “park,” a style focused on creative tricks on features within a terrain park. But Herman-Haywood missed the free flow of riding powder and soon moved to Washington, where she rode at Mount Baker.
“That was the coolest space in snowboarding,” she says. “It was one of the first mountains to allow snowboarding, and the culture there was more boarding than skiing. I fell in love with it. That mountain has been my biggest single influence in my level of riding,” she continues.
After moving back to Juneau for a job at a radio station, Herman-Haywood’s style of snowboarding had evolved from her time spent in the Lower 48. She was thrilled to be back home, and riding big lines in big mountains became her central focus. Herman-Haywood’s local connections allowed her access to helicopter-served riding, and she felt lucky to pursue big terrain in both Juneau and Haines.
Herman-Haywood now makes her living as a beadwork artist, a job that allows her time to pursue snowboarding when conditions are good, but is also an outlet for her creativity. Though she was less aware of it in her youth, Herman-Haywood recognizes that snowboarding also serves as a form of creative expression. “It’s cool to see how somebody chooses to ride a mountain,” she explains. “Your line down the mountains — your turns — it feels like you’re painting the mountain.”
In 2023, Herman-Haywood’s artistic expression and riding prowess earned her a part in a feature-length snowboard film, The Outliers, created by friend and Juneau local Mark Rainery. While many professional snowboarders travel to Alaska each spring to film, The Outliers focused on local riders and filmers in Southeast Alaska. Herman-Haywood’s part shows her hiking up through snow-covered trees before riding confidently at high speeds down a huge couloir just outside of Eaglecrest’s boundary.
Though she admits she enjoys being scared on top of a big line, Herman-Haywood is mostly focused on enjoying the “daily meditation of riding,” and trying to snowboard as many days as she can in a winter. She is in constant search of “the flow state that you get from being completely present.” She says, “Hiking a big line, riding it — the only thing you have to think about while snowboarding is going down the hill. That’s the ultimate disconnection from all the [distractions].”
Emily Sullivan is a photographer and writer focused on outdoor recreation, environmental wellness, and community empowerment. She is based on Dena’ina lands, where she can usually be found skiing, packrafting, or berry picking.
