Waring School Celebrates Grandfriend’s Day 2025 

November 5, 2025

What happens when generations come together in the classroom and as a community? At Waring School’s 2025 Grandfriends Day, the event was a delightful blend of shared stories, surprising observations, and a fresh look at education through the eyes of both students and their ‘grandfriends.’ 

Join us as we explore a day in the life at Waring School’s Grandfriend’s Day, where the past and present of learning beautifully intertwine.

Grandfriend's Day

Generations Connect 

A magical thing happens when generations connect, and at Waring’s annual Grandfriends Day, that blend of diverse perspectives fostered a profound sense of community.

This year, students invited a grandparent or an older friend to campus for a real peek into life at Waring School. Guests had the chance to sit in on classes, tour the buildings, and meet students’ friends.

The day kicked off in the All-School Meeting room, where grandfriends mingled over a light breakfast, all equally excited to spend the day with their Waring student(s). Head of School Tim Bakland offered a warm welcome and explained the unique elements of the Waring curriculum, including narrative evaluations (instead of letter grades), distinct styles of classroom engagement, immersive travel experiences, shared language and community activities. Tim then invited the grandfriends to reflect on their own educational experiences, setting the stage for a day of shared understanding.

Grandfriend's Day

A Grandfriend’s Perspective 

When Waring’s grandfriends responded to Tim’s invitation to reflect on their youth, a clear theme quickly emerged from their shared stories and comparisons of school “back then”: they all expressed their excitement for the different style of learning happening at Waring.

Many grandfriends were struck by the enthusiasm and motivation of Waring students to direct their own education. For instance, Core student Charlie’s grandfriends, Sue and Chip, were impressed by the students taking charge during a group activity—specifically, dissecting a historical poem in Humanities class. Similarly, Natalie’s grandmother, Sue, praised the openness of the experiences. At the same time, Abraham’s grandparents were awed by how each student could articulate their unique perspective in both small-group and full-class discussions.

Furthermore, several grandfriends were encouraged by the school’s no-phone policy, which frees students from the distractions smartphones pose to many in their generation. They also remarked on the authenticity of Waring students and their eagerness to learn from varied perspectives. This was a stark contrast to the grandfriends’ own school days, which they often characterized as strict and formal, marked by the traditional “seen and not heard” mantra. One grandmother explained that in her time, speaking out in class was discouraged, whereas Waring students are actively encouraged to communicate, collaborate, and challenge each other’s thoughts and perspectives.

Grandfriend's Day

Advice to the Next Generation 

Grandfriends Day came together in a perfect blend of the energy of the youth and the wisdom of experience. Many grandfriends offered advice to Waring students, even as they marveled at the unique opportunities offered at Waring, like the immersive travel experiences, shared foreign language experiences, thoughtful classroom engagement and experiential learning, such as Camping Trip, travel and End Term. 

Here are just a few nuggets of wisdom shared with our Waring students on Grandfriends Day. 

  • “Be true to yourselves,” and “Bring them into nature,” encouraged Edie’s grandfriends, Janice and Sheila.
  • “Don’t take yourself too seriously,” advised Carolyn and Bill, grandparents to Sera and Emily.
  • “Do your best, but be humble,” offered Ollie and Henry’s Pop Pop, Doug.
  • Carolyn and Paul stressed the importance of family and presence: “Spend more time with family,” and “Keep your face out of the computer.”
  • Noah’s grandmother, Zilda, summed up the contrast perfectly, remarking, “Everyone had the same path when I was in school. He is so lucky to have all these opportunities at Waring.

Grandfriends Day at Waring School is more than just an annual event; it’s a unique moment where the shared wisdom of experience weaves together with the excitement and energy of youthful learning. As the grandfriends departed, they left behind new memories and a renewed love of learning, confident that the Waring students are well-equipped to navigate the future with authenticity, enthusiasm, and a profound understanding of the world around them.

Grandfriend's Day