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Matthew Cunningham

Associate Director of College Counseling

Joined Milton in 2023

Matt is excited to join the Milton Academy community after three years as an associate director of college counseling at Sidwell Friends School in Washington, D.C.  Prior to his time at Sidwell Friends, Matt worked in college admissions for over eight years, first at Lehigh University in Bethlehem, PA and then at Vassar College in Poughkeepsie, NY.  At both Lehigh and Vassar, Matt was a key leader in their campus visit initiatives, including directing tour guide programs, as well as organizing open houses and admitted student programs.

Matt is enthusiastic about colleges and college admissions.  He believes that every student has a unique story to share and is looking forward to helping his students tell theirs.  As a college counselor, he has dedicated himself to supporting students and promoting their engagement and confidence throughout their college process.

Matt is a very proud graduate of Bucknell University, where he studied history and education, and he is looking forward to breaking out all his orange and blue clothing again.  He also earned his M.Ed from George Mason University and he is a lover of history, trivia, travel, food, and all things related to his favorite TV show, The West Wing.  During the 2023-2024 school year, he will be living with his wife in Wolcott House.