About

Faculty & Staff

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  • Photo of Miles Bailey
    Miles Bailey
    Admissions, Administration
    Dean of Admissions
    Year Appointed: 2018
    (860) 408-3015
    Emory University - B.A.
    Bio
     
    Passionate about the transformative power of boarding school education, Miles has dedicated his entire professional career to working with students and families. Prior to his appointment in 2018, he worked at Milton Academy for 16 years, gaining valuable expertise in all aspects of boarding school education. 
     
    Miles’ wealth of experience in not only admissions and financial aid but also athletics, development, residential life, advising, and coaching informs his work as both dean of admissions and a member of Westminster's senior leadership team. Miles oversees all aspects of enrollment management at Westminster while remaining integrally involved in the day-to-day operations of the admissions office and individual prospective families' school search processes. It is not uncommon to find him casually chatting with families in the waiting room, he reads every application received (with an uncanny memory for the details), and he delights in welcoming new students on Opening Day. He also plays a key role in positioning Westminster for continued institutional success through his leadership in activities, such as the school's pandemic response, search for a new head of school, and on-going strategic planning efforts. 
     
    Miles’ strong commitment to holistic, relationship-based education can be traced back to his time as a student at Westminster, making the opportunity to return to serve as dean of admissions particularly meaningful. As a student, Miles was a member of the John Hay Society, played basketball and lacrosse, and was on the student crew that helped maintain the cross-country trails. Even today, Miles remains deeply connected to both faculty and fellow students from his time as a student on the Hill.    
     
    Miles gets to know students and families well through the admissions process and enjoys maintaining those connections thereafter, catching up with parents at games and performances, chatting with students at family-style lunches and while on duty, and serving as an advisor. Miles and his wife, Susie, a science teacher, live in a faculty home with their daughter, Kate, and can often be found on campus with their black lab, Emmy, in the evenings and on weekends. In his free time, he enjoys cooking, fishing, travel, and spending time at the beach with his family.
  • Photo of Annie Berry
    Annie Berry
    Admissions
    Associate Director of Admissions
    Year Appointed: 2024
    (860) 408-3067
    Field Hockey
    Ice Hockey
    University of New Hampshire - B.A.
    University of New Hampshire - M.A.
    Bio
     
    Annie serves as associate director of admissions and shares her athletic expertise coaching the girls’ field hockey and ice hockey teams. She holds a B.A. in human development and family studies from the University of New Hampshire College of Health and Human Services, where she also earned a M.A. in kinesiology in 2024. She played on the Division 1 Women’s Ice Hockey team, serving as captain for two seasons. She was the recipient of the Hockey East Sportsmanship Award, a member of the National College Athlete Honor Society and earned many other collegiate accolades. Prior to attending university, she graduated from Tabor Academy, where she captained the field hockey, ice hockey and softball teams and was named All New England among other athletic awards.
    Annie loves ice hockey; her favorite pro sports team is the Boston Bruins. But she is also a baseball fan, loves country music and enjoys spending time with family and friends.

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In keeping with our support for a diverse community, Westminster abides by all applicable federal and state laws and does not discriminate on the basis of any protected characteristic, including race, color, religious creed, sex, sexual orientation, gender identity or expression, national and ethnic origin, ancestry and/or disability in administration of its educational policies, admissions policies, scholarship and loan programs, and athletic and other school-administered programs. Westminster admits students of any race, color, national and ethnic origin to all the rights, privileges, programs, and activities generally accorded or made available to students at the School. 
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