News
At the Winter Music Concert, Students Keep Hope Alive
As the days get shorter and the Boston air sinks well below freezing, this year’s annual Winter Music Concert offered songs on the theme of…
Gevvie Stone ’03 Receives NEPSAC Martin William Souders Memorial Award
Last month, during the annual meeting of the New England Preparatory School Athletic Council (NEPSAC), Olympian rower and physician Dr. Gevvie Stone ’03 received the…
5 Things to Know about Applying Abroad: U.K. Edition
Why limit your college search to just one continent? Each year, Winsor students submit applications to universities outside the United States, often in the United…
2025 Fall Athletics Banquet and Season Recap
With the latest season wrapped, varsity and JV athletes, families, and coaches gathered to honor the crew, cross country, field hockey, soccer, and volleyball teams…
Thankful for Grandparents and Grandfriends
Eager older learners streamed into the Wildcat Room ready to start their school day at Winsor’s annual Grandparents’ and Grandfriends’ Day event. The special program…
The College Counseling Process: Some Helpful Terms
The world of college admissions comes with its own language, which can be confusing at first. Understanding common terms can make the process clearer and a little less stressful. We’ve put together a glossary of frequently used words and phrases to help students and families feel more confident as they navigate the journey ahead.
Bearing Witness to History: A Conversation with Civil Rights Activist Dr. Valda Harris Montgomery
Civil rights activist Dr. Valda Harris Montgomery experienced many firsthand accounts of racism and segregation. But when asked when she first realized the full extent…
5 Ways Our College Counseling Team Gets to Know Your Students
Learn five ways we get to know Winsor students well before junior year, and how those insights become the foundation of the school letter that accompanies each application.
Local Author Sparks Rich Classroom Discussion
Local Puerto Rican–Bostonian author Elizabeth Santiago visited campus last week for a conversation with two sections of AP Spanish, a course for which students had…
Cross Country Wins 21st EIL Championship Title
Congratulations to the Winsor cross country team who finished first with a low score of 38 points to secure their 21st Eastern Independent League (EIL)…
Winsor Crew Finds Speed and Spirit on the Charles
More than 250 supporters gathered on the dock at the Winsor Belmont Hill Boat House to root for the Winsor crew at the 60th Head…
Three Decades of Under the Lights
A beloved Winsor tradition for over three decades, Under the Lights brings current and former faculty, students, alums, and parents to campus for a Friday-night…