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Greetings from the Hilltop
Heather Daly

A message from Pomfret's new head of school, Heather Daly.


In September of 2024, after a long and comprehensive search process, I received a call that would change my life. Pomfret trustee Daryle Bost ’89 phoned to share that I had just been selected as Pomfret’s next head of school. Shortly thereafter, Justin Klein ’65 and Tim Richards called to share their congratulations; I was unable to answer my phone, so they left voicemail messages. Since accepting this position nine months ago, I have returned to those messages time and time again, as a source of both pride and anticipation.

Today, the wait is over. As I pen this message from my new office in the School Building, I am reminded of all the amazing heads who came before me: William Peck, William “Bull” Olmsted, Jay Milnor, Brad Hastings ’68, and, of course, Tim Richards, to name just a few. As Pomfret’s thirteenth head of school, and the first woman to hold the position, I am proud to join their ranks in leading this remarkable institution.

First, I want to offer my sincerest thanks to Tim and Ann Richards for their warm welcome, and for the numerous hours Tim spent with me over the course of the past nine months in preparation for my arrival on the Hilltop. Their love, commitment, and care for this community are an inspiration to my husband, Brendan, and me as we begin our time at Pomfret.

In an increasingly complicated world in which adolescents are grappling to find connection and meaning, we know that small boarding schools like Pomfret — where students are known, loved, valued, and challenged — provide an unequaled opportunity for growth and development. Generations of Pomfret students have experienced the impact of a transformational boarding school experience under the care of an immensely talented and deeply committed group of faculty and staff members. 

I am grateful for the opportunity to build on this work alongside my new colleagues as we strive to empower our students to pursue lives of purpose and meaning. In addition, I look forward to partnering with Daryle Bost in his new role as chair of the Board of Trustees, and to working with former chair Justin Klein and the rest of the Board in their committed stewardship of Pomfret.

I promise to always be ambitious in my hopes for this School, to build upon the foundation that so many have laid. As your new head of school, I look forward to forging meaningful relationships with all members of the Pomfret community while striving valiantly in service to our students and our School.​​​​​​

 

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