Don Sheeley’s legacy lives on at Aspen sailing school, Ruedi Reservoir |

Don Sheeley’s legacy lives on at Aspen sailing school, Ruedi Reservoir

For the first summer in nearly 50 years, Aspen’s lone sailing program is navigating the waters without its leader at the helm.

Don Sheeley, a longtime Aspen local who died in January, started a children’s sailing school on the shores of Ruedi Reservoir in 1971.

In honor of Sheeley and his contributions to the community, which extend well beyond his aquatic endeavors, the city of Aspen on July 10 passed a proclamation to rename its sailing program the Don Sheeley Sailing School.

In a full-circle series of events, two of Sheeley’s former students — his daughter, Courtney Wyckoff, and Taylor Hale — now direct the sailing program, which the city Parks and Recreation Department has managed since the school’s inception.

Hale, who first joined the program as a child in the early 1990s, said leading the school after Sheeley is “one of the highest honors of my life.”

“Don Sheeley was just a really special, unique, stand-out guy. He made all the difference for so many kids in this valley, myself included,” Hale said. “He was really a pillar of the community.”

Without Sheeley at the reservoir, Hale seeks to emulate his predecessor’s teaching style, among other traits.

“Don’s whole philosophy, which I completely agree with, is you’ll learn it by doing it,” he said. “He always made us (students) feel that he trusted us.”

Wyckoff echoed Hale’s sentiment and said, “We (as students) all really appreciated it.”

“It wasn’t like a coach yelling at you. It was trial and error. We learned by doing,” Wyckoff said. “Through that, I think it was a lot more rewarding than someone holding your hand throughout.”

Hale said Sheeley’s style of teaching conveyed self-reliance.

“And with sailing, in particular, you have to have that,” Hale said.

The thought of returning to Ruedi without Sheeley — no less teaching a group of 10- to 14-years-olds on the open water — was daunting at first, Hale said.

“Honestly, I was pretty terrified,” Hale said. “Just the mental aspect of knowing Don was there (in the past). … He was the epitome of calmness and such genuine, deep confidence.”

Despite his initial trepidation, Hale said this summer at the school has been smooth sailing.

“It turned out that this summer’s class has been, honest to God, some of the best kids that I recall in the past five or 10 years. They’re fearless,” he said, and are thriving in spite of some “radically” unpredictable weather on the water.

Hale explained how unlike ocean sailing, which typically offers more predictable, less extreme conditions, “anything can happen” sailing on a lake, and even more so at high altitudes.

“It’s either dead calm or it is whipping, whipping, whipping, where we are the only ones out here,” he said.

Perhaps this is why one of Sheeley’s most remembered mottos at the school remains: “If you can sail at Ruedi, you can sail anywhere.”

For Hale, honoring Sheeley’s legacy at the school means more than passing along his wisdom.

“I don’t do anything that Don didn’t do. I park where he parked. I take the stuff out of the box where he took the stuff out of the box,” Hale said. “I just try and mirror everything (Sheeley) did, because he was the man.”

As the Don Sheeley Sailing School lives on, the city is “really impressed” with how they’re running the program, said Susan Arenella, who’s worked closely with the school in her 28 years at the Parks and Recreation department.

“It’s very special to me that this program is going to continue,” Hale said, “and that I get to be the one to instill the things Don instilled in me onto however many more generations come into this class in the future.”

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