Chesterbrook Academy Preschool in Naperville, IL

🎉 Chesterbrook Academy Celebrates 40 Years!
This year marks a very special milestone—Chesterbrook Academy is celebrating its 40th anniversary! For four decades, we’ve been providing nurturing care and quality early childhood education, inspiring young minds, and helping children build the foundation for a lifetime of learning. We can’t wait to celebrate this milestone together!
👉 See the article at the bottom to read more about this exciting anniversary and stay tuned for celebration details coming soon via Links to Home!

🔐 Door Code Change – September Update
As part of our commitment to safety and security, we change the entry door code twice a year. Our next scheduled code change will take place on Monday, September 8th.
All enrolled families will receive the new code via email and/or your parent communication app the week prior. Please be sure to keep the code confidential and avoid sharing it with anyone not authorized to pick up your child.
Thank you for helping us keep our school environment secure for everyone!
If you have any questions or do not receive the updated code, please contact the front desk.

🎭 Spirit Week – September 8th to 12th
Let’s kick off the school year with a week full of fun and creativity! Each day, students are invited to dress up according to the theme and show their school spirit.

Here are the daily themes:

• Monday: Disney Day – Wear your favorite Disney attire
• Tuesday: Crayon Day – Wear your favorite color from head to toe
• Wednesday: Sports Day – Wear your favorite sports team
• Thursday: Tie Dye Day – Get colorful and wear some tie dye
• Friday: Pajama Day – Come cozy in your favorite PJs

We can’t wait to see everyone’s spirit and creativity all week long!

🎃 Trunk or Treat & Open House – Save the Date!
Join us for our annual Trunk or Treat event on Saturday, October 25th from 10:00 AM to 12:00 PM in the school parking lot! Families are invited to decorate their trunks (Sign up sheet will be in the office) and hand out treats in a safe and festive environment.

🎉 This year, Trunk or Treat will also serve as our Fall Open House—so feel free to invite friends, neighbors, and anyone interested in learning more about Chesterbrook Academy! The event is open to the community, and we’d love to welcome both current and prospective families for a morning of festive fun.

Here’s what to expect:
✨ Decorated trunks with candy and goodies
👻 Kid-friendly costumes (no scary masks or weapons, please)
📣 Staff available to answer questions and provide tours

Want to decorate a trunk? Sign-up sheets will be posted in the lobby starting October 1st. We can’t wait to see you there!

🎪 Visit Us at Naper Settlement’s All Hallows Eve – October 17 & 18
We’re excited to announce that Chesterbrook Academy will be hosting a booth at Naper Settlement’s All Hallows Eve event on Friday, October 17th and Saturday, October 18th from 5:30 PM to 9:00 PM!

This fun, family-friendly Halloween event features trick-or-treating, themed attractions, live entertainment, and spooky surprises—all set within the historic village of Naper Settlement.

🎃 The Chesterbrook Academy booth will be representing all of our Illinois locations, so it’s a great chance to connect with families from nearby schools and share in the seasonal fun together.

📍 Location: Naper Settlement, 523 S Webster St, Naperville, IL
💲 Please note: There is an admission fee to attend this event. Tickets can be purchased through the Naper Settlement website or at the gate (while supplies last).

Don’t forget to stop by our booth to say hello and grab some treats. We hope to see you there!

Celebrating 40 Years: Chesterbrook Academy

Where Learning Lasts a Lifetime

Chesterbrook Academy proudly celebrates 40 years of educating, nurturing, and inspiring children from infants through eighth grade!

Since opening our first campus in 1985, we’ve had the privilege of guiding nearly 100,000 students through the most important steps of their educational journey. From preschool through middle school, we provide a supportive and challenging environment where students grow academically, socially, and emotionally. We help students build the foundation for their future success in school and in life.

A Legacy of Excellence in Education Since 1985

Chesterbrook Academy traces its roots to Chesterbrook Farm in Wayne, Pennsylvania, a historic property owned initially by Pennsylvania Railroad executive Alexander J. Cassatt. In 1985, Rocking Horse Child Care Centers of America (RHCCCA) transformed the property into a preschool, marking the start of Chesterbrook Academy. The school quickly distinguished itself by offering high-quality, curriculum-based preschool education rather than traditional daycare services.

This focus on curriculum and quality attracted a growing number of students and families to Chesterbrook Academy. In response to this demand, Chesterbrook Academy began expanding into new geographies while thoughtfully clustering schools together to facilitate higher-quality operations through shared support of the schools. Chesterbrook Academy began opening preschools beyond Pennsylvania in 1986, expanding into Illinois, New Jersey, North Carolina, Virginia, South Carolina, Florida, and Maryland over the following years. Building on the success and impact of our preschools, Chesterbrook Academy expanded to elementary and middle schools, providing older students with the same high-quality, challenging educational experiences.

Today, Chesterbrook Academy serves children from 6 weeks old through 8th grade. Though its name honors a historic farm, its legacy is rooted in delivering exceptional education to children. Chesterbrook Academy has fostered academic excellence, character development, and a lifelong love of learning in nearly 100,000 students across America since 1985.

What Sets Us Apart

At Chesterbrook Academy, children thrive because our classrooms combine academic excellence with hands-on, small-group learning and individualized support. Our teachers build strong relationships, celebrate each child’s strengths, and guide students through developmentally appropriate challenges that inspire critical thinking. Every day, children practice empathy, responsibility, and respect as they develop the academic skills and confidence needed to succeed in school and beyond.

As our preschool students develop into elementary and middle school students, this educational foundation allows them to consistently earn some of the highest scores among independent schools on the Comprehension Testing Program. This distinction reflects the strength of our rigorous curriculum, the expertise of our faculty, and the intellectual curiosity our students bring to every classroom. 

Learning with Purpose: A Curriculum That Connects

At Chesterbrook Academy, learning evolves as our students grow, from the foundation built in preschool to the independence and curiosity fostered in middle school.

In the early years, our Links to Learning® curriculum builds the foundation for future success. Through hands-on exploration, small-group activities, and personalized instruction, children gain early literacy, math principles, and problem-solving skills, while also learning to collaborate as good students and friends, and express themselves respectfully. Families stay engaged through our Links 2 Home® app, weekly newsletter updates, and ongoing communication.

As students move into elementary and middle school, our approach becomes more dynamic, student-centered, and appropriately rigorous. Students are empowered to dig deeper into concepts through collaborative projects, immersive experiences, and classes that inspire both creativity and confidence. Our teachers combine high expectations with meaningful support, ensuring every Chesterbrook Academy graduate is prepared to thrive in their next level of education. Chesterbrook Academy elementary and middle school students rise to the challenge of their academics, enjoy project-based learning, and participate in academic competitions in math and science.

40 Years and Just Getting Started

Over the past four decades, Chesterbrook Academy has remained committed to providing children with the educational experience they deserve. We’ve celebrated milestones, welcomed thousands of families into our school communities, and watched countless students take their first steps toward a lifelong love of learning.

From their first days in the classroom to the elementary years and beyond, our families share what Chesterbrook Academy has meant to them.

 “Upon starting kindergarten in the fall, it was clear to us how well prepared our son was thanks to the curriculum at Chesterbrook Academy. Not only was he academically prepared, he was emotionally prepared as well!” – Gabrielle K., former Pre-K parent

 “From the start, students explore STEM subjects in an engaging, hands-on way that sparks curiosity and builds a strong foundation. The teachers and administrative staff are the best we’ve ever encountered—passionate, professional, supportive, and genuinely invested in each child’s success.” – David J., 7th grade parent

As we look to the future, our commitment is stronger than ever. We’ll continue to grow, evolve, and innovate, always grounded in our belief that every child deserves to feel safe, engaged, and inspired.

To our teachers, families, and students, THANK YOU! You are the heart of Chesterbrook Academy. We are grateful to share this journey with you. Here’s to 40 more years of learning and growing together!