Santa Barbara’s Kevin Gleason Paints the Pacific Crest Trail

One painting, every day, for five straight months, while walking alone from Mexico to Canada. 

“It’s something I’ve always wanted to do,” said Kevin Gleason, who taught drawing and painting at Dos Pueblos High School for 26 years and is now hiking the Pacific Crest Trail (PCT). “When I retired from teaching and became a full-time artist last year, the space opened.”

The Tahoe-raised UCSB grad started his quest along the 2,652-mile route on May 3 near the Mexican border just south of Campo. He’s hiking about 20 miles a day to finish by October 1, hoping to beat significant snowfall in the Cascade Mountains.

But he must also stop every day to paint a six inch-by-eight-inch landscape in a 54-page sketchbook, planning to fill up three of them over his multi-month trek. “In 20 miles, the landscape changes so much,” said Gleason, who quickly picked up the trail name “QuickDraw” from other PCT trekkers. “All day long, I’m just waiting for that view that makes me want to take off the pack and sit down and spend a couple hours observing and painting.”

Gleason is painting in gouache — an opaque sort of watercolor — and plans to varnish and frame them when he’s back home in Goleta later this year. They will be part of an art show in the spring of 2027 at the California Nature Art Museum in Solvang. 

You don’t have to wait until then to see what he’s up to, though. Gleason is regularly posting his work to his Instagram account @kevingleasonart, and fans can message him to claim a piece if they’d like. 

An avid hiker and nature lover, Gleason hiked part of the PCT from Mount Whitney to Tahoe with his now-wife, Lauren, when they graduated from UCSB in 1996. That’s where he first met PCT through-hikers, and he’s been fascinated ever since. The idea burned in the back of his brain as he taught generations of Dos Pueblos art students from 1999 to 2025.

“It’s so much easier than it was,” said Gleason, explaining that they had to use a map and compass in 1996, whereas now everything is handled by an app called FarOut. Water sources, and their status, are listed, as are tent sites for camping, all updated by recent comments. 

“It’s fun when I’m feeling chatty to pull into a site where there are other hikers,” said Gleason, who’s met many twenty- and thirtysomethings from across the country and world. “There’s also a good amount of old guys like me.”

Wanting to come into each day with fresh eyes, Gleason didn’t research exactly what the route looked like in advance, so he was quickly surprised on day two, climbing 8,000 feet so close to the border. “I had no idea that I was gonna see pine trees that early,” he said.

He was about 440 miles in on May 26 when we spoke, as he chowed down his first-ever mulita from a grocery store in Agua Dulce. He said that the landscapes have regularly gone from cacti-laced desert to Santa Barbara–esque chaparral to lush green forests that people call “sky islands” — and then right back down to desert again.

“It definitely is living up to the name Pacific Crest Trail,” said Gleason. “It’s exceeding my expectations already.”

He expects to earn more than just 150 paintings out of the project. “There’s a lot of time to think on the trail as you walk along, to be able to reflect on my practice and try things out,” said Gleason. “I’m excited for not only my personal growth but also my growth as an artist with the space and time I’m gonna have.”

And he’s having a great time. “I feel so grateful to have this opportunity just to walk for several months and watch the landscape change and paint and be out in nature so much,” said Gleason. “Seeing every sunrise and sunset, and seeing the stars every night, it’s been really awesome.”

Seekevingleasonart.comand follow his progress on Instagram at@kevingleasonart.