Jessica Rosario-Calcaño P’28 P’33 Honored with Wendy Liff Flynn Award

The Board of Trustees held their annual meeting on June 2, 2026, and the program closed with the presentation of the Wendy Liff Flynn Award for Distinguished Service and Dedication to The Hewitt School. 

This award is named in honor of Wendy Liff Flynn P’05, chair of Hewitt’s Board of Trustees from 2001-2013. Established by the Board of Trustees, the award is presented annually to individuals, like Wendy, who demonstrate exemplary commitment and dedication to our students and our community. 

This year’s award was presented by Head of School Dr. Jennifer Zaccara to Former Trustee and Parents’ Association (PA) President Jessica Rosario-Calcaño P’28 P’33. 

Since 2015, Jessica has been a dedicated member of Hewitt’s parent and volunteer community. She has taken on multiple roles over the years, including serving as book club chair from 2017-2019, divisional class representative coordinator from 2021-2023, and a volunteer supporting merchandise sales and other initiatives. She also served on Hewitt’s Anti-Racism Task Force in 2020.

During the 2023-2024 school year, Jessica served as co-president of the Parents’ Association Board and went on to lead as PA Board president from 2024-2026. She was instrumental during our head of school transition, engaging the community and gathering feedback from parents while advocating for their voice in the process and ensuring continuity amidst a change in leadership.

Throughout her time at Hewitt, Jessica has generously volunteered her time in many large and small ways, contributing to the school community with dedication and care. Her leadership and commitment have left a lasting impact, and we are especially grateful that she extended her presidency to support the school as we searched for and welcomed our next head. 

Past recipients of the Wendy Liff Flynn Award include Valerie Mogul P’12 P’15; Joan Lonergan, former head of school; Laura Greene Meltzer P’21; Jo-Anne Williams Bilotti P’23; Julia Lewis P’21 P’26; Kate Tylis P’24; Candace Rabinowitz P’25 P’27 P’31; Amy Tarr P’25;  and Tracey Wallace ’73.