Alumni/Parents
Events
Throughout the year, Hillside School offers events in which parents and alumni can become better familiar with our school community, as well as with each other. At the same time, parents and alumni are invited to participate in and volunteer for special activities during the academic calendar year. The following are highlights of our annual events:
Parent Events
October:
- Fall Family Weekend: This event represents the first opportunity during the school calendar year when parents can learn more about our school community. During this weekend, parents can attend student classes and enjoy sports competitions. At the same time, they can hear about Hillside School plans and progress during a special Parent Reception (usually Friday night), sponsored by the Hillside Parents and Family Association (HPFA). The weekend continues Saturday with a morning of classroom visits and athletic games followed by a community luncheon.
- Grandparents/Grandfriends Day: This special occasion takes place on the Friday of Fall Family Weekend. Grandparents and Grandfriends are invited to attend student classes, view athletic games, and become informed about Hillside School at a special Grandparents/Grandfriends Luncheon.
November:
- Farm Day: Through this event, our Marlborough neighbors and members of our school community can witness and enjoy farm activities. In addition to becoming more familiar with our Farm's place in student learning (which includes environmental and agricultural education), Farm Day features such fun activities as live music, pony rides, free cider and donuts, games and a petting zoo!
- Parent-Teacher Conferences: The first Parent-Teacher Conferences for the academic year are usually scheduled in November. These conferences are parents’ opportunity to meet with your child’s teachers and become informed about his progress.You may want to learn more about how to make these conferences as productive as possible by clicking here.
December:
- Holiday Basketball Tournament: Hosted by Hillside School, this very popular seasonal event features spirited competition between several leading, junior day and boarding schools.
- Fall Awards Ceremony: Students are recognized for both personal and scholastic achievements for the fall term. Parents are always welcome to join with us in congratulating Hillside students for a "job well done."
February:
- Winter Carnival Day: Over the years, this event has proven to be a welcome respite from the long winter season. It features a wonderful array of special activities and interscholastic games enjoyed by students and parents alike.
March:
- Parent/Teacher Phone Conferences: Through this event, parents are informed about their students' progress through highly informative phone conferences. In preparing for these conferences, you may want to click here.
- Winter Awards Ceremony: As with the Fall Awards Ceremony, students are recognized for both personal and scholastic achievements for the winter term. Parents are always welcome to join with us in congratulating Hillside students for a semester of hard work and achievement.
May:
- Spring Fling Weekend: Welcome to spring! This fun and active weekend features many diverse, special activities including interscholastic games. Like Fall Family Weekend and Winter Carnival Day, Spring Fling is a wonderful way to enjoy our school community!
- Spring Play: Parents and others are welcome to attend this annual theatrical production in which students display their on-stage, performance skills.
- Prize Day/Graduation: This weekend concludes our academic year by honoring student achievements, as well as celebrating our ninth graders' successful conclusion of their Hillside School academic careers. Parents are both welcome and encouraged to attend events throughout the weekend including the spring awards and year end awards ceremonies, the headmaster's dinner for seniors and their families, commencement exercises and our graduation luncheon.
- Spring Awards Ceremony: Students are recognized for both personal and scholastic achievements for the spring term. Parents are always welcome to join with us in recognizing our boys for their personal and academic success.
Alumni Events
Alumni are always welcome to attend Hillside School events as well as visit our campus throughout the year. Hillside School takes genuine pride in the accomplishments of our graduates and we greatly appreciate hearing from alums on a regular basis. Along with school calendar activities, Hillside also features several annual events dedicated to our alums:
Volunteer Activities
Hillside cordially invites both our alumni and parents to volunteer for any of our regular or special school events. Your efforts can help ensure that our students benefit as much as possible from their Hillside School education. Volunteer activities can include anything from assisting with guest registration to scheduling events to working with Hillside staff in ensuring a positive experience for alumni, parents and other visitors to our school. In particular, we need volunteers to assist with the following calendar year activities:
September:
- School Registration Day
October:
- Grandparents Day
- Fall Family Weekend
November:
- Farm Day
February:
- Winter Carnival Day
May:
- Spring Fling Weekend
To learn more about parent or alumni volunteer opportunities, please contact Emily Kent, Director of Development, at: ekent@hillsideschool.net.

