Dr. Richard Calkins

Richard Calkins is the proud Superintendent of the Pocantico Hills Central School District in Sleepy Hollow, New York, where he leads with a vision rooted in innovation, equity, and whole-child education. With over two decades of experience in educational leadership, Richard is known for building strong school cultures that empower both staff and students to lead. Under his leadership, Pocantico Hills has become a model for how schools can welcome and engage all members of the community. He has championed initiatives that prioritize student voice, support teacher-led innovation, and foster authentic partnerships with families. From student-led professional development to tech-integrated leadership opportunities, his approach ensures that learning is collaborative, connected, and forward-thinking. A firm believer in leading by example, Richard works side-by-side with educators and families to ensure every child thrives, regardless of background. His leadership has helped transform his district into a forward-thinking, community-driven environment where everyone plays a role in shaping the future of learning.