Fall Family Weekend 2026

Aaron Case
Family weekends are a Millbrook tradition that gives parents the chance to view life on campus through the eyes of their students, once in the fall and again in the spring. Parents attend classes, walk the bricks to Assembly in the Flagler Memorial Chapel, eat lunch with students in the Casertano Dining Hall, and watch athletic games and practices.

Fall Family Weekend 2026 arrived on Thursday, as international families gathered in the Class of 2018 meeting room for a special dinner, and parents of day students met for parent-teach conferences. On Friday, the rest of the families arrived for a full day of activities—including meeting with the College Counseling Office to learn about college application processes and a panel Q&A with Millbrook’s deans. In class, students brought their families into their projects, giving presentations, working through math problems, and even sketching portraits of their parents in art class.

 
 
 
 
 
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During the final class block of the day, parents convened in the chapel to meet with Head of School Jonathan Downs ’98. Parents listened intently as Leo MacGowan sweetly serenaded them with a rendition of Adele’s “Make You Feel My Love,” and then Mr. Downs captured their attention with a State of the School address. His message revolved around recent insights on service and belonging shared with the community by faculty and alumni. “Teenagers are paradoxically self-centered and profoundly insecure,” he said. “So, when we can teach them to be committed to something bigger than themselves, they will be less self-centered and more grounded. They will be known, and they will be needed. They will matter.”

Friday finished with gatherings by form in Anthony House and Pulling House, followed by a food truck dinner by the baseball field and a boys varsity soccer game under the lights on the turf field. Energized by their families’ presence, the boys crushed Salisbury 6-0.



The weekend concluded on Saturday with more parent-teacher conferences and athletic competitions, after which the community headed off for a long weekend break, including a special trip to an indoor water park for international students, led by Jeff Smith and Sarah MacWright.

So much more than an event to check off the schoolyear schedule, Fall Family Weekend is a practice in community that brings students, faculty, and families together at the place that connects them all.

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