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Quintessential outfitter reflects on a lifetime in the backcountry

April 8, 2019 GMT

Roland Cheek clung to his dream even when his tenacity caused marital strife, threatened his family’s financial stability, lodged him crosswise with the U.S. Forest Service and pushed him to the edge of exhaustion.

Adversity made regular visits during his early years as an outfitter and guide in the Bob Marshall Wilderness.

Roland embraced tenacity again later when he decided to become a writer, even though he had limited formal education and had twice flunked English in high school.

They say love conquers all. And Roland Cheek’s long life seems to confirm the cliche’s veracity. It seems love prevails even when it’s occasionally saddle sore.

Roland said his wife, Jane, hit the roof when he disclosed plans to quit a good job with Plum Creek Timber Co. to embrace full-time guiding and outfitting in the Bob Marshall Wilderness.

It was September 1974. He’d been guiding part time for three years, taking clients out during vacations from work.

But, as Roland recalled this week, Jane came around.

“She pitched in like she has always done to do everything she could to make my dream work,” he said.

“We haven’t made any money, but I haven’t done anything I haven’t wanted to do for 55 years,” Roland said. “You are looking at a fortunate man.”

He gazed at a fire pit that crackled, spit and smoked. Jane sat nearby in the backyard of the home they share near Columbia Falls. Cheek, now 83 years old and comfortable in his eccentricities, wore shorts, a collared shirt and a pair of hiking boots.

The couple met in Roseburg, Oregon, and married in November 1954. Jane was 17. Roland was 19. Roland scheduled the wedding for the day after elk season.

His older brother had lit the fire beneath Roland’s love for the outdoors before leaving to join the U.S. Army Air Corps.

The death of Hillburn Cheek during World War II occurred under circumstances bitter and cruel.

Hillburn and fellow crew members of a B-24 Liberator bomber had survived dozens of perilous missions flown against Nazi Germany and two crash landings. They were homeward bound after Germany’s surrender when the plane crashed in Scotland in June 1945, killing everyone aboard.

“My brother’s death destroyed our family,” wrote Roland Cheek many years later.

Parents Viola and Hill Cheek split. Roland dropped out of high school and worked with his father in a logging and sawmill operation in Oregon.

Tragedy stuck again in July 1957 when Hill Cheek died after losing control of a loaded lumber truck. Not long after, Jane and Roland learned that their eldest child, a daughter, had severe developmental disorders that would require institutionalization.

Roland found a job in a plywood mill in Roseburg. Two co-workers who became hunting and fishing companions had spent time in Montana. Their descriptions of Big Sky country planted a seed in Roland.

In 1964, he and Jane moved to Montana after Roland landed a job in Columbia Falls with Plum Creek Timber Co. In time, he was promoted to safety director.

“Like wives all over the world, Jane bubbled with ambition for her husband’s continuing corporate rise,” Roland wrote in “Dance on the Wild Side,” published in 1999.

“We were sitting on top of the world. Only an idiot would rock such a splendid boat,” he wrote.

Roland rocked the boat when he started working part-time in 1971 as a hunting guide.

“I had never worked for an outfitter. I had never worked for a guide. The only thing I knew was to serve people the way I would want to be served, were I hunting with someone else,” he said. “I learned everything about guiding the hard way.”

Over time, the business, Skyline Outfit, offered guided hunting trips, float trips, wildflower trail rides, trips focused on geology and more.

Roland and Jane teamed up as the business grew, with Jane handling logistics, camp cooking and much more.

Her affinity for the Bob Marshall Wilderness grew, as did her backcountry expertise, and the couple’s love deepened.

Skyline Outfit focused on guiding smaller parties, an approach that limited income potential but yielded a host of satisfied customers - people who returned year after year.

Roland said an unexpected bounty was recognizing how many customers became friends.

“All the years I outfitted I had probably five people I would not take out again,” Roland said. “All the rest turned into friends.”

He once guided two brothers on a fall hunt. One shot a bull elk on the first day and spent the rest of the week lording it over his brother, creating a deeply unpleasant dynamic for everyone, Roland recalled.

Jane said one client was so fearful of encountering a bear that he toted a .44 Magnum handgun to the latrine.

Many clients were emotionally swept away by the spectacular scenery they encountered in the Bob. One woman afraid of heights crawled on her belly to the edge of a cliff to embrace the view. Tears streamed down her face, Roland said, as she contemplated the beauty before her and realized she’d likely never see this sight again.

Roland’s time in the backcountry led him to become an advocate for conservation and for the continued access to wilderness by people on horseback and their pack strings.

In 1973, he co-founded Back Country Horsemen of America. Over time, he served as president of the Montana Outfitters & Guides Association and was on the board of the Montana Wilderness Association.

In 1981, the Forest Service alleged that Skyline Outfit had knowingly engaged in a criminal act in 1980 by outfitting on National Forest land without a permit and without paying fees. Roland and Jane disputed the charge and won in federal court. But the legal fight had been expensive and uncertainty about Skyline Outfit’s outfitters permit had cost the company some bookings.

A national recession during the early 1980s also affected the business and, ironically, provided Roland the time to focus on realizing another dream - crafting a book of photos and text about the wilderness he loved.

Self-published in 1982, “Montana’s Bob Marshall Wilderness” became the first of 15 books authored by Roland. Six have been non-fiction and nine have been fiction.

Roland said he learned to write by being an avid reader of authors like John McPhee (non-fiction) and Patrick O’Brian (fiction). His best-selling book to date has been the non-fiction “Learning to Talk Bear.”

In the midst of all this, Roland and Jane raised two children, Cheri and Marcus. Cheri works now as a high school English teacher in California and Marcus is superintendent of a multi-million dollar remodel of the Phipps Mansion in Denver.

Meanwhile, Roland said that although Skyline Outfit did not leave him and Jane with saddlebags of money, the outfitting business yielded other riches.

He said Skyline Outfit made no secret that its trips could be tough, requiring miles of travel by horseback and occasional encounters with severe weather. He said potential customers who sought a luxurious, lodge-based, picture-window encounter with wilderness weren’t his target audience.

“The thing I miss the most is the pipeline to the wonderful people we met,” he said. “Our kind of people were looking for a tough trip back into splendid country.”

Reporter Duncan Adams may be reached at dadams@dailyinterlake.com or 758-4407.