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Penny in the Sky

A true local shows women how to soar


About Penelope Street ...

A dynamic skier with an exuberant flair and flash both on and off the snow, Penelope Street was a pioneer of the women’s freestyle movement in the early 1970s. A talented, aggressive competitor who was not afraid to catch air, Street learned upright jumps, front and back flips, and layouts as she excelled in mogul and aerial disciplines, mentored by the legendary freestyle skiers John Clendenen, Jack Taylor, and Bob Theobald. With her red hair flying, “Penny in the Sky” was a freestyle favorite: glamorous, risky, and confident. 

Penelope was an athletic wild child, smart, full of fire, fiercely independent, physically tough, and crazy about skiing and the mountains. She was born on the third floor of the Sun Valley Lodge in 1948, just two hours after her mother, Polly, a nurse, walked from Ketchum to Sun Valley. Bud Street, her dad, was a baker at the Challenger Inn who taught his two-year-old daughter to ski on Dollar Mountain. In grade school she was dropped off at Baldy at 7:30 a.m. so she could ride up with the ski patrol to help pack the bowls every morning. It was a pretty exhausting routine for a little kid, but apparently the reward was great. “I got to run the 103 steps to the Roundhouse,” she giggles, “where lunch every day was a chocolate roll and a chicken salad toast-tight.”

Penelope attended the old Ketchum Grade School that boasted about 20 kids per class. If you could ski, you raced, so she joined just eight or nine kids on the ski team who trained and ran gates on Penny Mountain. They were coached by Jack Simpson and Betty Bell. “Betty,” Street says, “was a great mentor to me as a little girl.” 

Penelope excelled in racing, but in high school she decided to just go skiing instead. On the weekends she skied, only going to school on Tuesdays, Wednesdays, and Thursdays, often writing her own excuse notes for skipping classes. In the spring of 1966, just one credit away from graduation, she quit school and headed for San Francisco, a naïve Idaho girl who learned to love the beat of the music and the freedom of the streets in Haight-Ashbury.

“I have learned to be in the present,
but it does make me laugh to look back like this
because it’s been so much fun!” -Penelope Street

When she returned to Sun Valley she modeled for Avventura, did a photo shoot for Seventeen magazine, and left again for Aspen, Lake Tahoe, and Lake Louise, ending up as the manager of a cattle ranch on Maui.

Then, in 1971, Penelope literally “jumped” into the earliest days of freestyle, talked into a team skiing event in Tahoe. “I really appreciate how we did it in those days,” she explains. “We were creative with lots of adrenaline, helping each other learn new stunts. Self-inventive, we were always having fun.” She adds with laughing eyes, “We were such free spirits and definitely not good role models!” The team was promoted in the media and in Warren Miller’s movies, but it was Penelope who graced the cover of Sports Illustrated doing her famous layout on a bluebird Baldy day.


Helping establish the International Freestyle Skiers’ Association, Street played a pivotal role for women by facilitating better press, sponsorships, and the prize money they deserved. Penelope was a consistent performer in North America and Europe who loved the control of mind and body that was needed to excel in freestyle skiing. But in 1976, after a competition in Crested Butte, Colorado, she retired when she saw some radical telemark skiing. It captured her untamed spirit and she never looked back.

Penny rocks a Daffy. Posing for a head shot (photo Kristin Cheatwood).


Extreme telemarking became Penelope’s new passion and she helped promote it by teaching and racing. She became a certified cross-country and telemark instructor and was sent by Ski Instructors of America to Europe and Scandinavia as a member of the first U.S. Demonstration Team.

“Basically,” she remembers, “we would just haul-ass on any slope with no tracks!” But she missed her family in Sun Valley, so she headed back home where she became a certified backcountry guide in 1983, working for over 25 years for Sun Valley Trekking

Penelope still loves the quietness of alpine touring, telemarking her way down radical terrain and pristine snow in the mountains she knows so well. She also happily chooses the peaceful creativeness of gardening for private clients during the non-snowy months. “I have learned to be in the present, but it does make me laugh to look back like this because it’s been so much fun! The biggest thrills of my life though,” she exclaims excitedly, “were jumping the cliffs at Squaw and telemarking the steepest, deepest powder in the Monashees.” -Julie Gallagher



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