By Mac McLean • The Bulletin

Jeanne Wolfe’s flight log looks like it was written by someone who never got tired of speeding down a runway, pulling back on her control lever and soaring through the air in a small passenger plane.

Every page in the leather-bound volume is full of entries detailing her flights — where she went, how long she was in the air, what type of a plane it was — since her first lesson on Jan. 31, 1957.

“On my first lesson, I saw two planes crash and fall into a schoolyard,” Wolfe said as she looked back to her first experience in the cockpit. “My instructor was shocked. … He thought I wouldn’t want to fly after that, but I still did.”

But the list of entries stops on Oct. 23, 1957, after about a dozen pages, each of which has enough space to record 10 flights. It doesn’t start up again until April 14, 2014, when Wolfe celebrated her 91st birthday by climbing into the cockpit of a single-propeller Cessna 4725 and rekindled her dream of getting her pilot’s license after a 57-year hiatus.

“It’s fun,” Wolfe said after a June 24 flight that took her from Bend to Prineville and back. “I haven’t flown for so long that I forgot a lot of things. But it’s all coming back to me now.”

The artist

Wolfe made a name for herself as an artist long before she climbed into the cockpit of her first plane.

“Even when I was a baby, I was drawing,” said Wolfe, who keeps a few sketches of babies and birds she did as a toddler in her apartment at the Aspen Ridge Retirement Community in Bend. “My parents encouraged it.”

Wolfe kept drawing as she grew up in Southern California and eventually put together a series of illustrations that filled in the otherwise empty pages that separated the sections of her high school yearbook.

She used these drawings to find a job at a local publishing company and later moved up the ladder until she was designing fashion and movie ads for the Los Angeles Herald-Express, an evening newspaper that merged with the now defunct Los Angeles Herald-Examinier in 1950.

During this job, Wolfe met James Raymond, an advertising executive she used to tease because he was colorblind and wore terrible clothes. She changed her mind one afternoon when she saw Raymond wearing the uniform he had from his days as a pilot with the U.S. Army Air Forces in World War II, and eventually she fell in love.

Wolfe and Raymond were married for 22 years, had one child and adopted two others — one of whom, Heidi Wiltse, lives in Bend — and raised them in their Southern California home.

She said Raymond also owned three planes and eventually convinced her to take up flying. In 1957, Wolfe almost got her pilot’s license but never took the test.

Wolfe and Raymond eventually divorced. Wolfe said the sting from this divorce stuck around for a while and she delayed marrying her second husband, Girdon Wolfe, for way too long because of it.

“‘Girdon’ means reward, and he certainly was that for me,” Wolfe said as she looked back on her second husband, to whom she was married for 36 years before he died in July 2007. “Anything I wanted to do was fine with him and he supported it.”

Wolfe said Girdon fully supported her decision to go back to college and pursue both her bachelor’s degree and a Master of Fine Arts degree when she was in her mid-50s.

He also helped her write and illustrate a children’s book — “The Wild World of Green,” which tells a story about a time when Wiltse wished she could grow wings and fly — that she published in 1983 when she was 60 years old.

The two even spent some time in Bend, where they ran a small store called The Timberwolf that sold some of her artwork, her etchings and her books along with other items in its Wall Street location.

Though there was one thing Girdon never let Wolfe do in all the time they spent together: fly.

“He loved to fly,” Wolfe said, explaining her second husband preferred first class to the cramped cabin of a single propeller plane. “But he didn’t want to fly with me.”

The pilot

Wiltse has a kind way of explaining why Girdon didn’t want his wife in the cockpit of a plane.

“He was a very safe type of guy,” Wiltse said while sitting in the Bend Airport’s lounge after her mother’s flight to Prineville. “He just wasn’t real comfortable doing the private pilot thing. … (He) wasn’t real keen on that.”

But Wolfe never forgot about flying.

Eventually, Wiltse got tired of saying, “Yeah, OK,” whenever Wolfe talked about how much she wanted to fly and decided to surprise the 91-year-old on her birthday with a flight lesson from Professional Air.

“(Wolfe) has such a good time,” said Jill Sweeney, a flight instructor with Professional Air who has worked with Wolfe since that first lesson. “I’ll step in when I need to, but for the most part she does it all.”

During their last flight to Prineville, Sweeney let Wolfe take the lead as she flew the Cessna over Powell Butte and the seemingly unending High Desert terrain. She noted that Wolfe wasn’t fazed by the choppiness of the air — it was windy that day as a storm was making its way through town — or the gliders that streaked across the sky.

Following Sweeney’s instructions, Wolfe touched her plane down at Prineville Airport’s runway for a quick landing before turning it around so she could take off and head back toward the southwest. The pair thought about doing a flyover at Sunriver but changed their minds so Wolfe could practice her takeoffs and landings at the airport in Bend.

“We got one hour in today,” Sweeney said when they stepped out of the plane so Wolfe could record her flight in her logbook. It was the fifth entry Wolfe had put in her logbook since she and Sweeney started flying again this spring.

Based on the entries in her log book, Sweeney said Wolfe had logged more than enough time in the plane to get a private pilot’s license in 1957. She had completed a handful of solo flights as well as a few longer-distance flights between Glendale, Calif., and Oxnard, Calif.

“She completed all her solo requirements 50 years ago,” said Sweeney, who wasn’t sure if Wolfe’s previous time would count toward a current license — no one’s ever asked her if a person can take a 57-year break from flight school and go back. But even if this time does count, there is one obstacle that stands in the way of Wolfe reaching her goal.

Before she can get her pilot’s license or even head out on her first solo flight, Wolfe needs to pass a medical exam that has been administered by a medical examiner licensed with the Federal Aviation Administration.

“It’s pretty basic,” Sweeney said, explaining the medical exam looks at a person’s general health and well-being, heart, hearing and eyesight. “But they can be pretty strict when it comes to the rules.”

— Reporter: 541-617-7816,