The Natural Convergence of Art and Adventure
If you find yourself on the skin track with splitboard guide Jessa Gilbert, you might notice her kick it into high gear and pull away from the group. Once you reach her, you’ll see something of an anomalous sight on a winter mountaintop: she’s pulled out a pad of blank paper, and in the five or ten minutes it’s taken you to catch up, she’s drawn the landscape you’re traveling through — a single line swooping across the page into peak, valley, forest, and perhaps a skier or two.
Sometime later — months, years, maybe — thousands of other people will come across that same drawing unfurled in color and grand scale on the side of a building in a bustling city center. They’ll share that same feeling of awe, wonder and connectedness with the wild that you felt on top of that mountain deep in the alpine. Those multitudes will be graced with a glimmer of that, too.
It’s an interface — a melding of art with sport, urban with wild — that Gilbert has alchemized both to live her own life and to expose others to the wonder she’s discovered in the mountains.
“I’m trying to take the most beautiful parts of these adventures back to where people are surrounded by concrete, locked into commutes, or feeling uninspired on those gray days,” Gilbert says. “I’m trying to create space where people can celebrate the colors and playfulness of being alive, and maybe inspire them to get out on their own adventures.”
Growing up in a split household in upstate New York with three brothers, Gilbert often escaped to the woods in search of quiet and began drawing and painting as a wordless release. She played three sports in high school and competed in snowboarding, so her art gravitated toward bodies in motion. But she never felt her passion for one world belonged in the other.
After a particularly vicious knee injury at age 25 robbed her ability to snowboard and run, she became less interested in drawing figures in motion. She embarked on a cross-country road trip while she worked to rehab her knee, eventually landing in Vancouver at the highway’s terminus. The Coast Mountains in British Columbia blew her East Coast mind, and — un-siloed from sport — she began drawing the landscapes to show people back home what it felt like to live in this colossal place where she’d decided to put down new roots. After living in the interior towns of Nelson and Revelstoke for a few years, she is now back on the coast where she calls Squamish home.
“And then the convergence of art and adventure became natural, as I got a bit stronger and started split-boarding and hiking again, and thinking about how I’m so blown away by these awe-inspiring vistas,” she says. “How do I take my materials with me, and slow down on the summit to try and articulate these gorgeous settings that we find ourselves in?”
Now, 33-year-old Gilbert funds her life through a mix of guiding at backcountry lodges — and her art. In 2023, she is hoping to become a fully educated splitboard guide — a rare commodity in the guiding world. Gilbert says she sees her artistic side as an asset in the outdoor industry: the same curiosity and attention to detail required to take in a landscape are critical skills in guiding.
For Gilbert, the pursuit of guiding is mostly another avenue for sharing the grandeur of mountains, “So other people can feel what it’s like to be here because it’s … it’s so inspiring. And I’d like to believe that inspiring people is the only way we’re going to actually make a change in this world.”
