Diana was born in 1964 in New York City. Where she was heavily influenced by her family members and their art collections. Later she would go on to the University of California in and graduate with a fine arts degree in 1988. Tremaine lived in Los Angeles for 14 years where she taught painting and drawing at Taft College and Chino’s Men’s State Prison.In 1999, in search of more space and greater access to the natural world that had become a great source of inspiration for her work, Tremaine moved to Bozeman, Montana where she now lives and works with her husband and daughter. In 2018, Tremaine was commissioned by Keeneland to paint retiring race horse champion Lady Eli.