Photos of Penny Pitou at the 1960 Winter Olympics in Squaw Valley by George Silk and Ralph Crane for LIFE.

It recently shocked me how new some of the women's winter olympic sports are. For instance, women's ski jumping is only being officially accepted into the Olympic program for the first time at the 2014 Winter Olympics in Sochi, Russia coming up in a few months (what!?). Facts like this make some of the pioneering women of Olympic sports only that much more impressive. Penny Pitou became the first American skier to win a medal in the Olympic downhill event at the 1960 Squaw Valley games, but before then, as a freshman in high school she had to ignore the no-girls rule and try out for the boys' ski team in disguise.

"I hid my hair under my hat and asked my friends to call me Tommy," she said. "I made the team and everything went great until I competed in a downhill race at New Hampton School. I crashed in front of a gate-keeper, my hat flew off and my hair came down. It's one of the few times in my life that I was at a loss for words."