College Counseling

Future Ready

College counseling is an integral part of our students’ education and begins when they arrive in Upper School. Our students develop critical thinking, writing, and interpersonal skills that will prepare them not only to be successful in the college application process, but ultimately to excel in college and beyond. Our experienced college counseling team stays current on admission trends and are involved in all aspects of the school community.

We also recognize the importance of personalized guidance in this process, and students are paired with a college counselor in the spring of their sophomore year. While discussions about specific colleges begin in junior year, we provide timely, relevant information to support students and families at all stages of this important journey. We welcome conversations with families and coordinate resources and programs covering specific topics such as financial planning, standardized testing, and course selection.

Our goal is not only to help Winsor students find the next education step that is right for them, but also to support their self-discovery as they pursue their aspirations beyond Winsor. As with all departments throughout the school, we work to help students learn how to "lead lives of purpose as responsible, generous-minded women.”

College Matriculation

In the last four years (2023–2026), Winsor graduates have most often entered the following colleges and universities:

Amherst College (6)
Bates College (3)
Boston College (7)
Boston University (6)
Bowdoin College (3)
Brown University (8)
Carnegie Mellon University (4)
Colby College (6)
Columbia University in the City of New York (4)
Cornell University (10)
Dartmouth College (4)
Emory University (10)
Georgetown University (10)
Hamilton College (4)
Harvard University (19)
Haverford College (4)
Johns Hopkins University (3)
Massachusetts Institute of Technology (12)
Middlebury College (4)
New York University (7)
Northeastern University (6)
Northwestern University (6)
Princeton University (5)
Stanford University (3)
Tufts University (9)
University of Chicago (3)
University of Massachusetts-Amherst (5)
University of St Andrews (6)
University of Virginia-Main Campus (3)
Vanderbilt University (3)
Wake Forest University (5)
Washington University in St Louis (4)
Wellesley College (3)
Williams College (3)
Yale University (4)

For Current Families

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

Office Hours: College Counseling Blog

Navigating the college application process can be exciting and complex, and at Winsor, no one walks that path alone. Office Hours: College Counseling offers families a window into the deep expertise and personalized approach that define Winsor’s College Counseling program. Here, you’ll find insights into the philosophy that guides our work, practical advice to help demystify each stage of the process, and tips to help support your student in finding their best-fit colleges. We hope these posts illuminate how our team empowers every student to approach this important milestone with confidence and curiosity. Interested in a specific topic? Check out our blog.

College Counseling Team
Jen Graham is a college counselor at Winsor School

Jen Graham

Director of College Counseling
Occidental College - B.A., Harvard Graduate School of Education - M.Ed.
Laura Iwanik is a college counselor at Winsor School

Laura Iwanik

Associate Director of College Counseling
Mount Holyoke College - B.A., Brandeis University - M.A.T., Harvard Graduate School of Education - M.Ed.
Mari Powell is a college counselor at Winsor School

Mari Powell

College Counseling Office Manager
Boston University - B.A.
three women posing for a photo
Winsor's College Counseling Team: Associate Director Laura Iwanik, Office Manager Mari Powell, and Director Jennifer Graham

“Winsor’s small size means the College Counseling team is able to learn about each student’s academic strengths, extracurricular interests, and personal goals over the course of their time at Winsor so that we can provide tailored guidance, helping them identify colleges that align with their aspirations and ensuring they are well-prepared for the application process. ”

Jennifer Graham,
Director of College Counseling