Like many musicians in the Sixties, Penny started her career as a folk singer in coffeehouses around Orange County, CA. She shared stages with many legendary artists such as Jackson Browne, the Nitty Gritty Dirt Band, Linda Ronstadt and the Stone Ponies,Jennifer Warnes, Mary McCaslin and others. In 1964 & 65 she sang in a bluegrass band with John, Bill & Alice McEuen (John then took Jackson Browne's place in the Nitty Gritty Dirt Band and the rest is history) and then formed a duo with Kathy Smith called the Greasy Mountain Butterballs which toured Vietnam in the fall of 1966. Upon returning, she opened the show for numerous artists at the Troubadour and Ash Grove in Hollywood.
In the spring of 1967, Penny rode up to San Francisco on the back of a Harley motorcycle and decided to stay in the bay area for a while. She performed in concerts and clubs all over the bay area including: the Fillmore, the Avalon, the Matrix and opened for bands such as Big Brother and the Holding Co. (Janis Joplin), Steve Miller, Quicksilver Messenger Service, 13th Floor Elevator, Chocolate Watchband, Jefferson Airplane and others. During the "Summer of Love", Penny played at the Big Sur Folk Festival and recorded her first album, "Penny's Arcade", for Buddha Records. (It eventually sold over 50,000 copies) After touring the U.S. promoting her album in the fall, she toured Europe in the winter of 1968, staying with George & Patty Harrison and recording at Apple Studios while in London.
On her return to the U.S., she decided to devote her time exclusively to songwriting for a number of years and studied voice with noted vocal coach, Florence Riggs. In 1975, she began to perform around Los Angeles with her jazz band, the Black Imp, and opened the show for Little Feat in concert. She wrote and performed commercials for Toyota's campaign to plant a tree for every car bought, Carnation Dairies, and produced a public service announcement for the Navajo Nation called "Black Mesa" to protest the misuse of the land around the Four Corners power stations in Arizona.
In 1977, while working with Emitt Rhodes on a record for Elektra, Penny joined Jimmy Buffett & the Coral Reefers. She appeared in the movie FM with the band toured the U.S. and earned a Platinum Record for her singing on Son of a Son of a Sailor.
In the late 70's & 80's, Penny went back to school and earned degrees in Music & Psychology from Antioch University, and then went on to Harvard University to do research in music & psychology eventually earning a doctorate in Education there. During the same time, she recorded and toured with many performers including: Art Garfunkle (Fate for Breakfast) Suzi Quatro, Danny O'Keefe,Yvonne Elliman, Jennifer Warnes, Albert Brooks, The Credibility Gap, Steve Gillette and earned a Grammy nomination for her work on Arlo Guthrie's album The Power of Love.
In 1990, Penny co-produced her second album, All Life is One. In 1993, she released another record, an album of songs based on the 1000-year-old Buddhist stories, the Jataka Tales. The album is called Songs of the Jataka Tales. In 1997, Penny and Molly Mason collaborated on the song "The Unbroken Thread" which is included on the CD, the Catskill Collection. She currently lives and teaches in the Hudson Valley of New York and is building a small studio in her house. Her most recent ventures include working on a series of Harmony and Background Vocal arranging CD's, a new CD of her own material, teaching at Swannanoa, one of the best music camps in the country, and producing the conference for songwriters: SummerSongs: A Songwriters Summer Camp.