Meet Dearcroft Montessori School's admission team at the Private School Expo: Halton-Peel (Oct 19). RSVP NOW
The big picture on Dearcroft Montessori School
We summarized the school ourselves
More than 50 years old, Dearcroft is one of the older Montessori schools in the country, founded in 1968 by Peter and Barbara Phippen. It also has very consistent history, now being directed by Gordon Phippen, son of the founders. All of that, while not essential to the delivery of a quality Montessori program, nevertheless underscores what parents and students value in the approach, namely a clear sense of community, family, cross-generational interaction, and a sense of tradition. The program hews very closely to Maria Montessori’s model, and also brings the community—both local and beyond—into the classroom. The student body is on the larger end for a dedicated Montessori school, and the benefits of size are apparent in the range of programs offered.
We questioned the school adminstration
1. Who are you, as a school?
"Established in 1968, Dearcroft is Oakville's original Montessori school offering programs from Toddler through to Junior High with three campuses in Oakville delivering exceptional Montessori Programs. Our North Campus offers an urbanized natural space, complemented by over 20,000 square feet of state-of-the-art classrooms. Our Satellite campus offers enriched Montessori programs for Toddler and Casa. Dearcroft is a fully accredited charter member of CCMA (Canadian Council of Montessori Administrators)."
Spacious, naturally lit classrooms
Computers & multi-media
Extensive athletics program / Montessori Model United Nations (MMUN) * NYC
Outdoor/experiential education
Performing arts stage/music/drama
Aboriginal/First Nation Studies
French from Preschool to Grade 8
Before and After Care
2. What do you do differently and uniquely well?
"At the core of our Montessori curriculum is a strong emphasis on peace education. This creates an environment of kindness and compassion where students are supported not only by...(more)
"At the core of our Montessori curriculum is a strong emphasis on peace education. This creates an environment of kindness and compassion where students are supported not only by our staff, but also by their peers as well. In short, a Montessori education creates wonderful opportunities for independence, creativity, and character development."
3. What tradeoffs has your school made to serve families in this way?
"A wonderful degree of innovation and natural design have driven the evolution of our school community. An excellent curriculum that goes above and beyond the public system...(more)
"A wonderful degree of innovation and natural design have driven the evolution of our school community. An excellent curriculum that goes above and beyond the public system requirements, where our graduates are positioned to pass entrance exams and be successful along their future learning paths. Our students have access to various programming including drama club, music, French beginning in our Casa program, and, intra-school sports competitions. Located on a stunningly natural, heavily wooded and truly beautiful historic estate short steps from Lake Ontario, Dearcroft’s campus is a remarkably inspiring and special place to grow and learn.
At Dearcroft Montessori, our commitment to the Montessori philosophy means that we intentionally prioritize a focus on the whole child, including hands-on learning, individualized growth, social and emotional development along with a deep respect for each child’s natural development."
4. What key junctures in your school's history have most shaped its present?
"Founded in 1968, Dearcroft is Oakville’s original Montessori School and one of the first independent schools Canada-wide. Under the consistent direction of the Phippen family...(more)
"Founded in 1968, Dearcroft is Oakville’s original Montessori School and one of the first independent schools Canada-wide. Under the consistent direction of the Phippen family and a highly experienced and dedicated staff for 53 years, Dearcroft is now led by owners Gordon and Lynda Phippen who have been members of the faculty for over three decades. Coinciding with our 40th anniversary in 2008, our affiliate campus (West Wind Montessori School) joined us at Dearcroft (1167 Lakeshore Road East). For an overview of the West Wind Montessori programs. Our graduates are grown with families of their own, and they are now sending their own children to Dearcroft. The vision of our school’s founders continues to flourish at Dearcroft, where countless young children have made the first steps of their exciting lifelong journey of learning for over half a century."
5. What type of student is a good fit for your school?
"At Dearcroft Montessori, we are dedicated to providing a nurturing and challenging environment that fosters a love of learning. When students and families share our values, the...(more)
"At Dearcroft Montessori, we are dedicated to providing a nurturing and challenging environment that fosters a love of learning. When students and families share our values, the Montessori experience becomes truly transformative. We believe that the best educational experience comes from a strong alignment between our philosophy and the characteristics of our students and families."
6. Under what conditions would you advise a family against choosing your school?
"Dearcroft Montessori is dedicated to fostering independence, creativity, and a deep love of learning. However, we understand that every family has different priorities when it...(more)
"Dearcroft Montessori is dedicated to fostering independence, creativity, and a deep love of learning. However, we understand that every family has different priorities when it comes to their child’s education."
7. To your knowledge, why do families choose your school over others?
"A wonderful degree of innovation and natural design have driven the evolution of our school community. An excellent curriculum that goes above and beyond the public system...(more)
"A wonderful degree of innovation and natural design have driven the evolution of our school community. An excellent curriculum that goes above and beyond the public system requirements, where our graduates are positioned to pass entrance exams and be successful along their future learning paths. Our students have access to specialized programming including drama club, music, French beginning in our Casa program, and, intra-school sports competitions."
8. How would you characterize your school's image amongst the public?
"Celebrating over 50 years, Dearcroft continually proves to be a highly respected leader in education. Our experienced staff takes great pride in offering a warm and engaging...(more)
"Celebrating over 50 years, Dearcroft continually proves to be a highly respected leader in education. Our experienced staff takes great pride in offering a warm and engaging environment for students. Dearcroft provides programs for Toddlers (starting at 18 months – 3 year olds), Casa (2.5 – 5 year olds), Junior Elementary (6 – 9 year olds), Senior Elementary (9 – 12 year olds) and Junior High (13 and 14 year olds). We offer an intimate learning experience within our supportive and close-knit community. The comprehensive and methodical training of staff, excellent ratios and long-term relationships allow us to focus on all aspects of each child’s development."
9. What aspect of your school is underappreciated?
"One of the most underappreciated aspects of Dearcroft Montessori is the depth and intentionality of our individualized learning approach. While Montessori education is often...(more)
"One of the most underappreciated aspects of Dearcroft Montessori is the depth and intentionality of our individualized learning approach. While Montessori education is often associated with independence and hands-on learning, the meticulous planning and expertise that go into guiding each student’s unique journey can sometimes go unnoticed. Our approach ensures that each child moves through their educational journey at their own pace, mastering concepts deeply before moving on. This organic progression fosters intrinsic motivation, resilience, and a genuine love of learning—qualities that stay with them for life.
A key component of this journey is our emphasis on Expedition Education—learning that extends beyond the classroom walls. Whether through hands-on environmental studies, community-based projects, or immersive historical and cultural experiences, students develop a global perspective, leadership skills, and the confidence to navigate real-world challenges."
10. What might families find surprising about your school?
"For 25 years Dearcroft/West Wind has been Canada’s leader in elementary experiential education. Our award-winning Expedition Education Program established in 1996 has been an...(more)
"For 25 years Dearcroft/West Wind has been Canada’s leader in elementary experiential education. Our award-winning Expedition Education Program established in 1996 has been an innovative and exciting extension of our curriculum. Through an integrated and highly ambitious travel-based experience, our West Wind Junior High students have had the opportunity to explore Canada from Coast to Coast."
11. What improvements or changes has your school made recently?
"Dearcroft Montessori has grown into three thriving campuses, each dedicated to providing high-quality, authentic Montessori education in Oakville."
"Dearcroft Montessori has grown into three thriving campuses, each dedicated to providing high-quality, authentic Montessori education in Oakville."
12. How will your school change in the next 5 years?
Discover our 4,000-square-foot classroom, complete with a live green wall, floor-to-ceiling windows, a Music and Art Studio, a Science Discovery Area, and an outdoor balcony with green space for lunch and work. Enjoy a quiet mezzanine workspace with a library. Located in Oakville’s Urban Village, our school offers access to hiking trails, Lions Valley Park, 16 Mile Creek Sportsplex, and interconnected green spaces like Memorial Park. With stylish interiors and proximity to the Go Station and urban amenities, our school provides a vibrant, inspiring learning environment."
Watch our parent interview with Katherine & John Vellinga to get the inside scoop on what it’s like to have a child attend Dearcroft Montessori School.