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A Q and A with Betsy Duff

We sat down with the incoming Board of Trustees President Betsy Duff to learn more about her interests, what brought her to Chestertown, and her hopes and dreams for Radcliffe Creek School.

Radcliffe Creek School Board of Trustees
Board President, Betsy Duff

How long have you been involved with RCS?

A little over five years. I originally learned about and became involved with Radcliffe as a member of an Advisory Council in 2018. Knowing that I had served as a trustee and alumni advisor to independent schools in the past, then-Board President, Susan Newton-Rhodes, invited me to participate. I was delighted to find a way to learn more about RCS and to contribute to the school’s future planning in a small way. A few years later, Meg Bamford encouraged me to join the Board of Trustees.


Why did you decide to serve on the Board of Trustees? 

My husband, Jim, and I bought our second home in Chestertown in 2013. As we began to spend more time in the area, I was hoping to find ways to connect and give back to the community. With my prior board experience, I saw joining Radcliffe’s board as a good way to help out. Recognizing the challenges all schools faced after COVID and seeing both the unique characteristics and transformative impact of our school, I became determined to do my part to ensure Radcliffe Creek’s success.


What is your favorite thing about Radcliffe Creek School?

I love the mission, the dedication of the faculty, the creativity and flexibility of the curriculum, but, more importantly, I love that Radcliffe truly does change students’ lives. I have seen several really moving examples of this in recent years, including during Thrive Night when children who previously found public speaking both undesirable and unattainable, perform with glee and abandon on a stage in front of a large audience.

While this scene might unfold in any elementary school, it is the looks (and tears of joy) on the Radcliffe teachers’ faces that underscore how far these kids have come on their personal learning journeys.


What do you hope to accomplish in your new leadership role? What

priorities do you see for RCS in the next three years?

As Board President, it will be my privilege to work closely with Peter Thayer in his third year as Head of School, and then to welcome our next Head in 2025. Identifying, hiring, and welcoming our next school leader into the community will be a top priority for the board for the next several years. In addition, we will continue to emphasize the health of our school community through higher student admissions growth and retention of our outstanding faculty. We will ensure the school’s financial flexibility and sustainability through fundraising and strong financial management. Additionally, we will oversee the School’s strategic direction as we move forward into its next chapter under new leadership.


What are you personally most passionate about?

Three things top the list: #1 - my family, #2 - education, and #3 – community service. Following in my mother’s footsteps, I am a lifelong volunteer and, for the past thirty years, my focus in service and philanthropy has been on education. I have served on independent school and nonprofit literacy and arts organization boards with a goal to provide leadership, fiscal oversight and governance in the field. With its foundational impact on one’s educational success and opportunities in life, I firmly believe that literacy is a basic human right - for all children, in all geographic areas, with all types of learning styles. I am forever grateful to my parents for prioritizing education throughout my life and for fostering in me the belief that an investment in education is the greatest gift. Jim and I, likewise, have made our children’s schooling our highest priority and are honored to focus our philanthropic efforts on schools and access to excellence in teaching.


Tell us more about you and your background.

Jim and I were initially introduced to Chestertown in the mid-1980s by my close childhood friend, Tracy Stone, and her husband, Jim – the innkeepers of The Inn at Mitchell House. Through them, over the years, we grew to appreciate and enjoy the upper Bay and the beauty and opportunities of Kent County. We were really excited to become neighbors in 2013 and have traveled to Chestertown almost weekly since then. We have loved joining the community!

Originally, I am from St. Louis, Missouri, and my ties to that city still run deep, as my father, now 92, and my sister and her family, are all there. In addition, I remain connected to my K-12 alma mater, and several organizations influenced over the years by my late mother who was a beloved St. Louis community leader.

I moved to the D.C. area in the early 1980s and met my husband, Jim, soon thereafter. We have two grown children, Patrick and Maggie, each of whom currently resides in California, working in technology and sports construction, respectively. Our lives often seem as though they revolve around our pets: a 12-year-old labrador (Bailey) and two cats (Phoebe and Otis). In terms of hobbies, in addition to art and music, Jim and I both enjoy boating on the Bay, Jim wishes he played more golf, and I do my best to squeeze in a yoga class, pickleball game, or a swim workout, whenever possible.



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