Linda Casterano - Featured Speaker at Millbrook's Annual Alumnae Event

The first time I drove down School Road, it was dirt, and I was filled with dread. It was in the winter of 1990. Drew and I had been invited to campus by the search committee, which was charged with selecting Millbrook School’s 6th headmaster.

I recall only a few details of our 24-hour visit – probably because I was not thrilled to be there. At the time, we were comfortably settled at Loomis Chaffee. We had just moved from a campus house back into the dorm, where I was the dorm head. I loved my work there in admissions and financial aid. We had a great group of friends, and there was a large number of faculty children – no shortage of playmates for Alex and Tyler, ages 7 and 4. Life was good! That said, Drew was interested in pursuing a headship at a boarding school, and we agreed that was something we both wanted for him, for us, and for our family. But so soon?
I reminded myself that this was part of a plan that we had set back in 1980 when Drew was planning on law school and studying for the LSATs. Sensing that his heart wasn’t really in it, I told him that I saw a huge upside to working in boarding schools and that he shouldn’t feel any obligation to pursue law school on my part. In just a short time in our married life, I had discovered how much I enjoyed living and working in a community among adolescents and smart, interesting adults who were committed to educating the hearts and heads of their students. I embraced how my professional and personal life were intertwined. I was certain we could make not only a living but a life together of this work and be very happy. 

Back to that first visit to Millbrook. Drew and I spent much of the day apart. I recall being on the verge of tears most of the day. I met with Rita McBride, the dean of faculty, a group of women who had children about the ages of Alex and Tyler, and some student leaders, including Julie Rosenberg ’91, who was the school president our first year. Come full circle, Julie’s daughter, Clio, will enter Millbrook’s third form this fall. Del Shilkret, the business manager, gave me a driving tour of the area. Eight miles to the village of Millbrook? Yikes! How could this ever work? I grew up in the suburbs. I was perfectly happy living on a school campus on the edge of a town where we could walk to the library, the movies, and Baskin and Robbins. After a full day of meetings, Drew and I thanked our hosts, hopped into our car, and headed up School Road. I was relieved to hear him say, “Don’t worry, I’ll never take that job.”

The search committee skillfully kept the conversation going, and things moved quickly. Of course, Millbrook offered Drew the job, and we accepted. The deciding factor was the insight that John Ratte, Loomis’s head and Drew’s mentor, provided to Drew and me. In a remarkable coincidence that would change the course of our lives, John served as the head of the visiting committee for Millbrook’s 10-year accreditation during the 1989-90 school year, which gave him an “insider’s” view of the school. He encouraged us to accept Millbrook’s offer. The school had good bones and a compelling history and mission. With John’s blessing, we were heading to Millbrook, and, as they say, the rest is history.

I tell this story because 31 years later I could not feel more different as I drive down School Road. The dread has been replaced by excitement and gratitude, which begin with the view of the chapel steeple from route 44. I take in the beauty of the countryside and the sights and sounds of the wildlife, which make their habitat in the fields and marshes. I wave to the students, teachers, and faculty children whom I may encounter along the way. There is a rhythm to the drive which I have come to love. This is my community. This is my home. This is my school. How living here for 31 years has changed my perspective! And, of course, no one, including members of the search committee, ever imagined that we would stay for just over three decades.

So what’s changed? The short answer is a lot, starting with the paving of School Road. The enrollment has doubled, the campus has grown to 800 acres, the square footage of buildings has tripled with the addition of Mills, Holbrook, Hamilton, Koenigsberger, the maintenance plaza, the new counseling center, the business office, and, yes, Casertano Hall. Every existing campus building has been renovated, and the endowment has grown from $5,000,000 to nearly $65,000,000.  I would be remiss if I did not mention the improvements to the towns of Millbrook and Millerton and the impact of the internet with the ease of online shopping! Those are the facts, and they’re important.

But the real answer is that along with witnessing this progress, I have been fortunate to have participated in it and, I like to think, contributed to it in small ways.

When I arrived on campus in July of 1990, I still had my reservations, but Drew and I had committed and were in this together. I was seven months pregnant, and my primary concern was transitioning Alex and Tyler to a new home, new schools, and new friends. Our family received a warm welcome – faculty families stopped by to introduce themselves, bearing gifts of food and flowers, offering playdates and dinners, and suggestions for things to do.

As the school year got underway, I quickly experienced the public nature of Pulling House – faculty meetings, parent receptions, even a movie crew moved in to shoot a scene for the film “Regarding Henry.” I had only been home two days after giving birth to Will, our third child, when alumni gathered at Pulling House for fall reunions. I believe that weekend we hosted a trustee and his wife in the school’s guest room located in the house – the first of many - trustees, alumni, guest lecturers, and teacher candidates who would stay with us. I think it was a year later that Drew revived the third form reading, which took place weekly in the living room.

While it may have seemed like baptism by fire that September, over the years I really never minded people coming in and out of the house, especially if it was a scheduled event. I will always be indebted to Maureen King, the director of food service, who was sensitive to the fact that Pulling House was our home as well as the school’s primary social venue. She shepherded me through these first few years with humor and grace and always made me look good as Millbrook’s First Lady. With the construction and renovation of several new buildings over the years and most recently the dining hall, there are far fewer events held in Pulling House. And I admit, at times I miss that. 

Early on, I decided that I wasn’t going to work for at least the first year at Millbrook. The combination of Drew’s new job and a new baby were certain to make our lives even busier, and I sensed that settling ourselves in was going to be a full-time job. Although Drew and I had worked together effectively – and happily - in the admission office at Loomis Chaffee, I thought it would be better to strike out on my own and have my own identity when the time was right. Being at Millbrook was still an experiment, and I wasn’t ready to make a deeper commitment.

When I think about my role at Millbrook over the last 31 years, I see it as two distinctly different experiences. The first half - from 1990-2004 - I operated more behind the scenes. I call these my “Stand By Drew” years. I did my best to balance managing a family of five with a career in development with positions at Dutchess Day School, Browning Associates, and Indian Mountain School. I was able to carry on my duties at Millbrook, hosting and attending school events, but I was pretty removed from the daily schedule, especially during the eight years at Indian Mountain as I departed the Millbrook campus each day at 7:30 a.m. with our own kids who were students there as well as a number of faculty children whom I volunteered to transport.

These years were busy ones with our children. With a more flexible schedule and one that did not require work on Saturdays, I took the lead coordinating their various activities, with the exception of youth hockey, which Drew carved out time to coach. I will say that even with all the demands on his time as headmaster, he never missed an important event in our children’s lives.  

Drew’s early years were especially challenging, and the 24/7 commitment sometimes seemed relentless. Still, we made many friends in the greater Millbrook area and beyond through our children’s schools, youth sports programs, the Millbrook Golf and Tennis Club, and my work at Indian Mountain. We enjoyed the opportunity to meet people and have a social life outside of the school community. Our children also benefitted tremendously from these associations, though living on campus was great fun for them. As fac brats, they reveled in their run of it. They loved attending games and performances; they had a number of favorite babysitters over the years, including Jon Downs '98. 

While my time at IMS was very satisfying and rewarding on many levels, after eight years I was feeling ready for a change, and I started to feel a pull to become more involved at Millbrook. Serendipitously, Bob Anthony was looking for someone to step in for one year as annual giving director, while the current director took a leave. As I had the requisite skills, including knowledge of the computer program, it seemed like a great fit at the right moment. That I was the headmaster’s wife was actually helpful as I dealt with parents and alumni. I enjoyed that year, and I think it was probably the first time I really felt I was making a personal investment in Millbrook and taking ownership of the school. Thus began my “Standing With Drew” years.

My comfort with working at Millbrook led me to accept an opening in the admission office as associate director of admission and director of financial aid. I remain grateful to Cindy McWilliams for offering me this opportunity and for Jon Downs for sticking with me when he succeeded her as director of admission, and Meg Grover when she succeeded Jon. My investment in Millbrook increased with every prospective student I interviewed as I walked the talk – regaling the virtues of Millbrook School. I was now on the front lines – at admission receptions and in the offices of secondary school counselors at feeder schools. I was able to combine some of my admissions travel with Drew’s trips to meet with alumni – whether it be Washington DC, Denver, and San Francisco or Hong Kong, Shanghai, and Hanoi. I enjoyed meeting alumni and parents and forging relationships, which I hold to this day – and hope to maintain in this next chapter of our lives. 

I also had 3-4 advisees each year, which was great fun and provided a real window into student life. Working with these students was a good reminder of what we do and how well we do it and helped to inform my work in admissions. 

During these last 17 years, through my greater involvement at the school and my deeper commitment to being “all in,” like our students, I have reaped the benefits of being known and needed. I have felt – and now share - the pride our faculty and staff take in being a part of the school community, advancing the school’s mission, and preparing our students for lives of meaning and consequence. I see the strong school spirit among our students and the love they have for Millbrook, which they carry with them as alumni. I have witnessed and experienced first-hand the care, compassion, and generosity of this remarkable community as we have celebrated together in moments of great joy and mourned together in times of terrific loss.   

Through this journey I’ve grown tremendously, had a lot of fun, made many friends, and learned some valuable life lessons. While it was not love at first sight, it has been a 31-year romance and a truly fulfilling partnership with Drew. When we close the door to Pulling House for the last time in June and make the drive up School Road, it will be with hearts full of love and gratitude for a place and people we will forever hold dear – and with a certain joy and satisfaction knowing that we are leaving Millbrook School better than we found it. 

Thank you for listening to my Millbrook story. I am eternally grateful to all the people who played a role in my journey, including many of you. I refrained from naming more individuals as there are just too many. I hope I have expressed my gratitude to them along the way, but I also plan to make every effort to re-state my appreciation in the next few months. 
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