"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)."
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. 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.
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.
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 over 55 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.
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.
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.
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.
Celebrating over 55 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 – 2.5 year olds), Casa (2.5 – 5 year olds), Junior Elementary (6 – 8year olds), Senior Elementary (9 – 11 year olds) and Junior High (12 and 13 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.
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.
For over 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. An integral part of our East Coast Expedition is an exciting collaboration with Dalhousie University’s Ocean School, where students will engage in hands-on learning that brings ocean science to life. As part of this immersive experience, students will visit Dalhousie’s renowned marine research facilities and spend time with Dr. Chris Harvey-Clark—a marine biologist, veterinarian, and leading expert in ocean conservation. Through guided exploration and interactive sessions, students will deepen their understanding of ocean biology, climate impact on marine ecosystems, and coastal sustainability.
Dearcroft Montessori has grown into three thriving campuses, each dedicated to providing high-quality, authentic Montessori education in Oakville.
Over the next several years, we envision our school continuing to grow as a deeply connected, fully aligned Montessori community that supports children from their earliest years through adolescence. Guided by our core mission—to nurture independent, confident, and compassionate learners—we will focus on creating greater continuity, strengthening academic and social–emotional support systems, and enhancing the experience of families across all campuses. In September of 2026, our North Campus will operate from Toddler to Junior High.
Hear directly from Dearcroft Montessori School community as they share insights.
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