At Winsor, the college search is viewed as a process that is an extension of the overall education taking place in the classrooms, on the athletic fields, and in each venue on-campus where active learning takes place.
And just as each student's learning path is unique, each student's college search process is an individualized journey, one in which we guide our students to a greater understanding about themselves and their aspirations. Along the way, critical thinking and decision-making skills that are a part of every Winsor classroom experience become essential tools in researching and evaluating the wide variety of post-secondary opportunities available. And throughout that personal journey, Winsor's college counselors are here as advisors, allies and advocates, endeavoring to offer appropriate support and counsel at every step. With the focus and responsibility placed clearly on the shoulders of the individual student, we offer support and guidance that will lead to meaningful discoveries and appropriate opportunities. 

College Choices 2016-2020

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  • In the last four years, Winsor graduates have most often entered the following colleges and universities:

    Amherst College 4
    Barnard College 10
    Boston College 8
    Boston University 9
    Bowdoin College 6
    Brown University 8
    Carnegie Mellon University 3
    Colby College 4
    Columbia University in the City of New York 9
    Cornell University 3
    Dartmouth College 7
    Davidson College 4
    Emory University 3
    Georgetown University 4
    Hamilton College 6
    Harvard College 26
    Haverford College 3
    Johns Hopkins University 7
    Massachusetts Institute of Technology 6
    Middlebury College 4
    New York University 8
    Northwestern University 6
    Princeton University 4
    Stanford University 5
    Tufts University 12
    University of Chicago 6
    University of Pennsylvania 5
    University of Southern California 3
    Vassar College 4
    Washington University in St Louis 7
    Wellesley College 4
    Wesleyan University 3
    William and Mary 3
    Williams College 3
    Yale University 13
    In the last four years, Winsor graduates have also entered many other leading schools:
    Two each to: American University, Bentley University, Carleton College, Claremont McKenna College, Colorado College, Duke University, Elon University, George Washington University, Harvey Mudd College, Kenyon College, McGill University, Mount Holyoke College, Scripps College, Syracuse University, University of Michigan-Ann Arbor, University of North Carolina at Chapel Hill, University of Notre Dame, University of Richmond, University of St Andrews, Vanderbilt University
    One each to: Bates College, Berklee College of Music, Brandeis University, Bryn Mawr College, Bucknell University, California Institute of Technology, Case Western Reserve University, Colgate University, College of the Holy Cross, Connecticut College, Dickinson College, Fordham University, Franklin W Olin College of Engineering, Georgia Institute of Technology-Main Campus, Guildhall School of Music and Drama, Howard University, Lehigh University, Northeastern University, Oberlin College, Pomona College, Pratt Institute, Salve Regina University, Santa Clara University, Smith College, Southern Methodist University, Swarthmore College, The American University of Paris, The University of Texas at Austin, Trinity College, Tulane University of Louisiana, United States Naval Academy, University of Cambridge, University of Connecticut, University of Massachusetts-Amherst, University of Massachusetts-Lowell, University of Virginia-Main Campus, University of Wisconsin-Madison, Wentworth Institute of Technology, Worcester Polytechnic Institute
To learn more about the College Counseling Office please contact: Helen Grassi College Counseling Assistant(617) 912-1350

College Counseling Team

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  • Craig Allen, Director

    Craig Allen arrived at Winsor as the school's new Director of College Counseling in 2016. Previously, he directed college counseling offices at three boarding schools for twenty years (Phillips Exeter Academy, Hotchkiss School, and Hill School), led similar efforts at a day school (briefly), and served as Associate Director of Admissions at Duke University, his alma mater. (He also spent some seven years in public school classrooms teaching Honors and A.P. History classes before ever getting into the selective college admissions world.)  Along the way, he became a veteran of various duties, school-related responsibilities, and activities, from coaching and dorm duty, to singing and competing in student/faculty quiz bowls. With his youngest child recently graduated from college and now gainfully employed, Craig and his wife of almost thirty-eight years now focus their attention on a different generation - their parents. Duke basketball and a couple of cats serve as nice distractions.

  • Jennifer Graham, Associate Director

    Jennifer Gustin Graham joined the Winsor community in 2003 after eight years in college admission and independent-school college counseling. In addition to serving as the Director and Associate Director of College Counseling, she teaches English, served as an Upper School Class dean for 12 years, and occasionally plays the viola with the Winsor orchestra. A native of Washington state, Jen is a graduate of Occidental College and the Harvard Graduate School of Education. Her two daughters, after years of spending family vacations touring college campuses, are now in college themselves, so Jen and her husband spend their free time skiing, hiking, and entertaining their Boston terriers, Tilly and Olive.
  • Helen Grassi Vest, College Counseling Assistant

    As College Counseling Assistant, Helen Grassi Vest becomes the 'utility player' for our college counseling team, handling any and all challenges thrown her way. Most importantly, Helen is the office's technology guru and the person who is most responsible for managing the submission of applications, the collection of data, and as our first point of contact for many. She is an important resource for our students and keeps in touch with the many college representatives who work with us. She also plays a variety of roles in the larger Winsor community, coaching squash and tennis, serving in various administrative capacities, and recently serving as a seminar leader in the school's Independent Learning Experience (ILE) program. A graduate of Hobart and William Smith Colleges, Helen joined the office in 2010.

College Counseling Calendar

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