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Hope Ostrowsky

2024 Cheshire Academy Town Scholar Announced

Hope Ostrowsky surprised by CA “party bus” with
four-year scholarship

Cheshire resident Hope Ostrowsky thought she was going out with her parents for an early dinner on March 7. But when she walked outside, she found herself the center of a celebration in her driveway complete with a Cheshire Academy minibus, the Cat mascot, balloons, an acceptance package, and a bevy of congratulations from CA administrators, faculty, and staff, including Head of School Julie Anderson P’19,’23. Ostrowsky is the 2024 recipient of the Cheshire Town Scholarship. 
This prestigious award, which originated in 1938, provides one incoming ninth grader from Cheshire a full, four-year scholarship to Cheshire Academy.  

“Following a competitive application process, we are so excited that Hope will be joining the Cheshire Academy community as our 2024-2025 Town Scholar! She exemplifies every characteristic we look for when we evaluate our Town Scholar candidates,” said Rich Ferraro, associate director of financial aid and associate director of community relations. These qualities include scholarship, citizenship, ambition, and leadership, among others. 

Originally from Michigan, Ostrowsky moved with her family to Cheshire in 2019. Enjoying a close community and her teachers at her current middle school, she is a competitive volleyball (club) and basketball (AAU) athlete with aspirations to play on the collegiate level. Outside of school and athletic pursuits, Ostrowsky enjoys music and concerts, especially Bruno Mars. 

No stranger to the school’s campus, she has visited numerous times for events like open houses and sports games and is thrilled to be joining the community. Hope follows in her brother’s footsteps as a CA Cat – Joseph Ostrowsky ’21 completed a postgraduate year at the Academy as a basketball standout. 

Prospective students interested in applying for the Cheshire Town Scholarship for must have been a Cheshire for at least one year, and complete an interview, admission application, and essay detailing why they should be the next Town Scholar by the school’s application deadline of Feb. 1. They must also have completed the eighth grade by June 30. Partial scholarships are offered to runner-up applicants.  


For more information, visit the Cheshire Academy website at cheshireacademy.org/scholarships. 

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