After several successful seasons with the U.S. ski team, Penny Pitou competed at the 1956 Winter Olympics, but with little success. She continued to ski the European circuit, however, and by 1958 had gained a reputation as one of the world’s top skiiers. Her European experience also included becoming fluent in several languages and climbing the Matterhorn – without a guide. In 1959 Penny Pitou began to win downhills and giant slaloms with frequency and was a gold medal favorite at Squaw Valley in 1960. She just missed the gold in two races at Squaw Valley but her name made the headlines there in another way. She was linked romantically with Austrian star, Egon Zimmermann, and they would later marry and then divorce. After retiring from competition, Penny Pitou began to run ski schools in New England. She also served as a fashion consultant to the ski industry and a participant in ski shows and ski promotions. She started Penny Pitou Travel, one of the largest travel agencies in New England, which specialized in arranging ski trips and tours to Europe.