In 2024, Gabriella C. Calicchio was named the fifth Executive Director of the Oregon Shakespeare Festival (OSF), bringing more than 30 years of arts leadership experience to Ashland. A dynamic and visionary leader, Gabriella’s career has been shaped by her passion for arts advocacy, strategic planning, organizational growth, and community engagement.
Before joining OSF, Gabriella served as Director of Cultural Services for Marin County, where she oversaw the Marin Center, Marin Center Presents, the award-winning Marin County Fair, and the Marin Cultural Association (MCA). Under her leadership, MCA became the leading arts organization in the County, fostering a unified voice for the arts through the Marin Arts and Cultural Plan. Her efforts positioned the Marin Center as a vibrant cultural hub that embraced and served the entire community.
Gabriella previously served as Chief Executive Officer of The Walt Disney Family Museum, founded by Diane Disney Miller to preserve and honor her father’s legacy. Before that, she served as Managing Director of the Children’s Theatre Company (Minneapolis, MN), one of the country’s most prominent children’s theatres and the only one to receive a Tony Award®️ for outstanding regional theatre. Earlier in her career, Gabriella held a succession of executive positions in the Bay Area, including Managing Director of Marin Theatre Company (Mill Valley, CA), where she successfully restored the organization’s financial stability, cultivated long-term funding sources, helped develop a new series for emerging playwrights, and expanded outreach efforts to underserved communities in Marin City and the Canal neighborhood of San Rafael.
Her extensive career also includes leadership roles as Executive Director of Diablo Ballet (Walnut Creek, CA) and Director of Theater Operations at the Smith Center at Ohlone College (Fremont, CA). Gabriella began her career at Harvard University’s Sanders Theater Box Office and has since built a reputation for inspiring leadership and a commitment to artmaking.
Gabriella holds a Bachelor of Arts in Drama and Dance from Bard College and a Master of Arts in Arts Administration and Education from Lesley University. She is an alumna of Stanford University’s CSI Fellowship for Executive Leaders in the Arts, the National Arts Strategies program on strategy and finance, and the prestigious Wilder Foundation’s James P. Shannon Leadership Institute. Gabriella and her husband are proud parents of two college-aged children, Isabella and Elia.