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At Winsor, the college counseling process serves as an extension of a student's learning experience and values "intellectual curiosity, authentic engagement, and personal integrity.”
Our highly experienced and collaborative college counseling team encourages students to utilize the strong critical thinking skills they have developed at Winsor to investigate and evaluate a range of options where they will flourish.

Every student's journey through the college selection process is an individual one. Our goal is not only to assist Winsor students in finding their best next educational steps but also to support their self-discovery as they prepare to "lead lives of purpose as responsible, generous-minded people.” 

List of 4 items.

  • Winsor School Profile

  • College Matriculation

    In the last four years (2019–2022), Winsor graduates have most often entered the following colleges and universities:

    Amherst College (4)                                       
    Barnard College (6)                                        
    Boston College (13)
    Boston University (8)
    Brown University (8)
    Carnegie Mellon University (3)
    Colby College (4)
    Columbia University (5)
    Cornell University (3)
    Davidson College (3)
    Duke University (4)
    Emory University (7)
    Fordham University (3)
    George Washington University (4)
    Georgetown University (8)
    Hamilton College (3)
    Harvard University (15)
    Johns Hopkins University (3)
    Massachusetts Institute of Technology (6)
    McGill University (3)
    Middlebury College (3)
    New York University (6)
    Northeastern University (4)
    Northwestern University (4)
    Princeton University (3)
    Stanford University (3)
    Syracuse University (3)
    Tufts University (9)
    Tulane University (3)
    University of Michigan-Ann Arbor (3)
    University of Pennsylvania (5)
    University of St Andrews (3)
    Washington University in St Louis (9)
    Wellesley College (7)
    Yale University (7)
    2 each to:
    American University, Bates College, Bentley University, Bowdoin College, Brandeis University, Colorado College, Dartmouth College, Elon University,
    Kenyon College, Mount Holyoke College, The University of North Carolina at Chapel Hill, Oberlin College, University of Richmond, Santa Clara University, University of Southern California, Southern Methodist University, University of Virginia, Wesleyan University, University of Wisconsin—Madison                                                                     
    1 each to:
    The American University of Paris, Berklee College of Music, Bryn Mawr College, Carleton College, University of Chicago, Claremont McKenna College, University of Connecticut, Duke Kunshan University, Fashion Institute of Technology, Georgia Institute of Technology, Guildhall School of Music and Drama, Harvey Mudd College, Haverford College, College of the Holy Cross, Macalester College, University of Maryland-College Park, University of Massachusetts-Amherst, University of Massachusetts-Lowell, University of Notre Dame, Occidental College, Franklin W Olin College of Engineering, University of Pittsburgh, Pomona College, Rhode Island School of Design, Rice University, Salve Regina University, Scripps College, Smith College, Stonehill College, Trinity College, Vassar College, University of Vermont, Wells College, Wentworth Institute of Technology, William & Mary, Williams College, Worcester Polytechnic Institute                     
  • For College Representatives

    Please check back. Content to come soon.
  • For Current Families

    Visit the College Counseling Resource board on WILD for helpful handouts, class resources, and more.


List of 3 items.


    M.Ed Harvard Graduate School of Education
    B. A. Occidental College

    Jennifer Gustin Graham joined the Winsor community as the director of college counseling 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, advises the student government and the Jewish students club. A native of Washington state, Jen is a graduate of Occidental College in Los Angeles and the Harvard Graduate School of Education.

    B.A. Mount Holyoke College
    M.A.T. Brandeis University
    M.Ed Harvard Graduate School of Education

    Laura Iwanik joined the Winsor community in 2023 as the associate director of college counseling. Previously, she worked in college admissions at both Harvard and Georgetown Universities. She began her career teaching high school history before transitioning to higher education for eight years. At Winsor, she serves as a member of the Upper School Student Life team. Laura is a graduate of Mount Holyoke College, Brandeis University, and the Harvard Graduate School of Education.


    B.S. Boston University

    Mari Powell joined the Winsor community in December 2022 from The Park School. She has worked in various capacities at other local independent schools, including Brooks and Phillips Andover. Mari and her family also spent a number of years living and working at The Cate School in California, where she assumed the role of college counseling administrative associate. A graduate of Boston University, Mari is familiar with the city and with the culture regarding education. She is experienced in dealing with standardized testing issues, college financial aid forms and processes, service programs, and special summer opportunity programs.