Stephanie McCaine of Katonah, NY, is a third-generation Town of Bedford resident. She attended KLSD public schools through middle school and graduated from The Harvey School in Katonah. After earning a B.A. in Psychology from Skidmore College, she pursued graduate study in music therapy in Philadelphia before beginning her career in education and admissions.

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A former music therapist turned educator and strategist, Stephanie has dedicated most of her professional life to helping students, families, and schools navigate growth and change. She spent more than two decades in admissions and enrollment leadership at colleges across New England and the mid-Atlantic, including serving as Director of Admissions at SUNY Purchase for ten years. She later helped launch a public charter school and led enrollment strategy, marketing, and diversity initiatives for independent schools before founding Hamlet Education Group, an independent educational consulting practice based in Bedford. Through Hamlet, she provides personalized guidance to students and families navigating high school, college, and early career transitions, drawing on her deep experience in both higher education and local community life.

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As an engaged citizen and community connector, Stephanie has served in a wide variety of volunteer and leadership roles throughout Bedford. She has been a youth soccer coach, Girl Scout troop leader, Bedford Community Theatre board chair, and an active member of the Bedford Democratic Committee. She currently serves as Deputy Supervisor for the Town of Bedford, where she is known for her thoughtful, data-informed, and collaborative approach to leadership.

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Stephanie lives in her childhood home with her husband, Robin, and her mother. Their daughter, Shelby, is a college student. Living under the same roof she grew up in makes her both nostalgic and deeply aware of how far Bedford has come—and how much further there is to go.

 

Stephanie McCaine is running again because she knows that thoughtful, inclusive leadership matters—and because she loves this town. She wants to continue building a Bedford that works for everyone while staying true to the character that makes this community special.