Making Memories at Marlborough’s Sleepover and Retreat Days

Marlborough’s Middle School and Upper School dedicated time to bonding and building friendships during the annual Middle School Sleepover and Upper School retreat day. Designed to bring classmates together at the start of the year, set intentions, and connect through engaging activities, these traditions provide meaningful experiences for students at every grade level.

A Night Under the Stars
The Middle School Sleepover transformed Marlborough’s campus into the ultimate sleepover destination, complete with activities galore and rows of colorful sleeping bags. Students in Grades 7 through 9 packed their coziest pajamas and favorite pillows to spend an unforgettable night at School—a cherished tradition unique to the Middle School community. 

Students spent the afternoon bouncing from nail painting stations to crafts tables, jumping in the pool, and playing on Booth Field before enjoying a smorgasbord of food for dinner. The In-N-Out truck was an obvious favorite, and students also piled plates high with pizza, tacos, fruit pops, and more. As the sun set, the students took to the stage for their time to shine during the much-anticipated Lip Sync Battle. 

Advisory groups rehearsed lip sync performances in the week leading up to the Sleepover, and their hard work paid off during one of the night’s most spirited moments. 8th Grade Dean Caitlin Benson captured the joy and camaraderie that makes it her favorite part of the night: “The students get super excited and they do a great job being inclusive of their peers. I always smile when I see the more reserved students up there dancing away with their Advisory. We even have a dance party while they wait for the judges to deliberate; the joy is palpable.” 

As the evening wound down for the night, students settled into Caswell Hall for a movie night before heading outside to arrange their sleeping bags under the stars. Come morning, dedicated fathers and guardians awoke the sleepy middle schoolers with a hearty pancake breakfast. 

Students departed campus with their bellies full, friendship bracelets on, and sleeping bags tucked under their arms—carrying with them unforgettable memories of laughter, creativity, and connection during their magical night on campus.

Building Community Through Adventure
While the Middle Schoolers headed home to rest, the Upper School students arrived ready for a meaningful retreat day with their classmates.

The Class of 2028 ventured off-campus for team-building activities and a high ropes course, using the day to bond and set intentions for their first year as members of the Upper School. As they tackled rock walls and extreme heights, the Sophomores supported one another fiercely, transforming initial fears into shared triumphs throughout the day. Dean of the Class of 2028 Katherine Pollock reflected on the day’s success: “It provided the opportunity to bring the class together and build community with one another through fun and adventure.”

The Class of 2027 embarked on their own off-campus adventure, participating in an “Amazing Race” style competition with their classmates. The challenge encouraged problem-solving and teamwork while exploring new corners of Los Angeles. 

Teams split up; one group tackled Little Tokyo while the other explored Santa Monica. They each faced different challenges: some raced to solve puzzles that would lead them to a final showdown where they “saved the city from monsters,” while others worked to thwart a “rogue spy.” Between strategic thinking and collaborative problem-solving, students enjoyed treats like matcha and ice cream. 

The day concluded with reflections on the lessons learned through the competition, preparing the Class of 2027 for the year ahead with sharpened leadership skills. Ilyana Contreras, Dean of the Class of 2027, noted that after the retreat, “we have a group of students who lead with action, empathy, vision, and analysis.”

While the rest of the Upper School was exploring Los Angeles, the Senior class remained on campus to reflect and plan for all of the exciting milestones awaiting them in their final year at Marlborough. 

Their day centered around the theme “Team26,” beginning with a thoughtful discussion on finding meaning within a team or community with the Director of Educational and Counseling Services Dr. Morgan Duggan. This concept of team came to life as Seniors paired up for a bounce house obstacle course on Booth Field with a twist: partners remained connected throughout the course. 

The race provided plenty of laughter and memorable moments as students navigated the course while literally tied to a teammate, creating a powerful lesson in support, communication, and togetherness. The Class of 2026 also dedicated time to college essays and yearbook pages, as well as making important decisions about Senior year traditions like Graduation and mascot presentation.

The Seniors enjoyed a day that was both entertaining and purposeful, strengthening their class identity as they begin their final year together.

These annual traditions were thoughtfully designed with one goal in mind: cultivating fun, friendship, and genuine connection across every grade level. With the support of the incredible Marlborough faculty, students were able to come together and make enduring memories beyond the classroom walls. The result was a powerful sense of community that sent students into the weekend feeling connected, energized, and prepared for the year ahead alongside their classmates.