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An Oakville Tradition with a National Reputation for Excellence.
Canada’s Leader in Elementary Experiential Education

Three locations to serve you:

An Oakville Tradition with a National Reputation for Excellence. Canada’s Leader in Elementary Experiential Education.

Three locations to serve you:

Delivering bold and inspiring curriculum for over 55 years in Oakville.


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Our Mission

Dearcroft Montessori School’s mission is to provide our students with the opportunity to develop and nurture their individual academic and social strengths in a safe and motivational learning environment.

Within classically structured and fully equipped Montessori classrooms, immersed in a naturally inspired setting, our students experience an exciting, well balanced curriculum.

Dearcroft is the third oldest independent school in Oakville and we remain one of Canada’s longest serving Montessori Schools.

Introduction to Dearcroft Montessori

Founded in 1968, Dearcroft is Oakville’s original Montessori School and one of the first independent schools Canada-wide. Our campus is situated on a beautiful, historic two-acre property, within walking distance of downtown Oakville. We have remained family owned and operated, now run by second-generation Montessori educators. Dearcroft is accredited by the Canadian Council of Montessori Administrators (CCMA) and a founding member of the Oakville Independent Schools. Celebrating 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. Keeping in-line with Montessori best practices, all of our classrooms feature:

  • Individualized, child-centered programs
  • Enriched programming, tailored to meet the needs of each student
  • Multi-age environments
  • Low student/teacher ratios
  • Hands-on, experiential learning
  • Individual and small-group lessons

Q & A Dearcroft /West Wind Montessori School

Dearcroft Montessori School
Where was the idea of Dearcroft Montessori School born?

Our school, established in 1968 by Peter & Barbara Phippen, was originally named Centennial Montessori School, commemorating Canada’s hundredth birthday in 1967.  That year, Peter Phippen studied Montessori in Bergamo, Italy under the guidance of Mario Montessori, Maria Montessori’s son.

With the goal of creating a unique, child centered, truly exceptional Montessori school in Oakville, upon their return, the Phippen family opened what is now the longest serving Montessori program in our community.

In 1976, our school was renamed Dearcroft and moved to our Lakeshore Road East campus.  Dearcroft is the third oldest independent school in Oakville and we remain one of Canada’s longest serving Montessori Schools with an international reputation for excellence.

What sets Dearcroft and West Wind Montessori apart of the rest?

Our exceptional staff take great pride in offering a warm and engaging learning environment for students in programs from toddler to grade 8.  We empower students to become responsible, productive, and caring citizens with a strong sense of social justice and a comprehensive understanding of environmental stewardship.  Together, our staff, students, and parent community foster a positive environment both in and beyond the classroom.  This develops students who are firmly grounded, with a powerful sense of self, and compassion for others and the world in which they live. 

At Dearcroft, our Montessori trained teachers are deeply committed to excellence and the continued development of our school community.  Dearcroft Montessori is a CCMA charter member school, and our Director Gordon Phippen has served as both chair and CCMA consultant. Additionally, Gord Phippen and Anna Campbell, our Director of Programming, are both CMTE certified trainers. 

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. 

West Wind Montessori Junior High offers an integrated, experience-based curriculum intended to motivate and inspire!  Our challenging and enriched two-year program is designed to prepare our graduates for a successful transition into the high school of their choice and the world beyond. 

For over two decades, West Wind Junior High has encouraged academic independence, interaction, character-building, project management, critical thinking, and leadership skills.  Our mission is to help youth discover themselves and their full potential in our unique Montessori environment that inspires excellence, empowering them to engage in and ultimately shape their world. 

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.  Exploring our country’s magnificent geography, visiting UNESCO World Heritage Sites, Provincial and National Parks, and world class museums.  From the majestic Pacific beaches of Vancouver Island to magnificent Yukon landscapes, across the vast Prairies and amazing Great Lakes, along the mighty St. Lawrence River through historic Quebec and the Maritimes, to the incredibly rugged, Atlantic coast of Newfoundland, we have explored so much of Canada’s remarkable geography over the years on these unforgettable journeys of learning.  Additional Expedition Education trips within our continent have also taken us to Alaska, the Everglades and Florida Keys.  Our West Wind Jr. High students have also had the opportunity to participate in the international Montessori Model United Nations (MMUN) conferences held in NYC for the past 15 years.  Adventure can inspire us, unlock hidden potential, broaden our horizons, awaken our spirits, and refresh our senses.  No classroom resource can compete with this. 

How does a Montessori education differ from traditional learning models?

Maria Montessori was a remarkable educator and a woman very much ahead of her time.  Born in 1870, she became Italy’s first female doctor and worked extensively in education. She developed a unique “scientific pedagogy” that is known as the Montessori Method and has now been practiced around the world in thousands of schools for over a century.  Montessori classrooms are carefully prepared learning environments designed to inspire creative thinking and support and encourage individual learning styles.

At Dearcroft and West Wind Montessori, the comprehensive and methodical training of staff, excellent student to teacher ratios and long-term relationships allow us to focus on the individual child’s development in full alignment with Montessori best practices.  All classrooms feature: individualized, child-centred programs, enriched programming tailored to meet the needs of each student; multi-age environments; low student-teacher ratios; hands-on; experiential learning; individual and small group lessons and enriched music and French programing.

Dearcroft and West Wind curriculum goes well beyond Ministry of Education requirements and our high level of academics prepare our students for success.  This level of preparedness helps to ensure our students obtain not only their first high school of choice but also success in their post-secondary education opportunities and career paths beyond.

In today’s world, how can a child benefit from a Montessori education?

One of the greatest benefits of a Montessori education is building real-life skills that carry over when it is time to enter the workforce. Problem-solving, creativity, teamwork, and responsibility run through the veins of a Montessori child.  Collectively, grace, courtesy, empathy, and peace education, coupled with off-site learning opportunities  helps to create independent, self-confident and motivated learners. 

A Montessori education consciously designs social communities and educational experiences that cultivate the child’s sense of self-awareness, tolerance and empathy.  Montessori learning environments allow for the respect and celebration of the individual spirit within people of all ages. 

Our highly experienced staff takes great pride in offering a warm and engaging environment for their students.  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.  Keeping in-line with Montessori best practices, all of our classrooms feature: 

  • Individualized, child-centered programs 
  • Enriched programming, tailored to meet the needs of each student 
  • Multi-age environments 
  • Low student/teacher ratios 
  • Hands-on, experiential learning 
  • Individual and small-group lessons 
    What makes Dearcroft and West Wind Montessori School unique as an educational institution?

    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 specialised 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.

    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.  Within the past several years, Grace and Jamie, the grandchildren of founders Peter & Barbara Phippen, have graduated from Dearcroft and moved on through high school into their university years.  We have a number of second-generation families! 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.

      Are you part of the CWELCC (Canada Wide Early Learning and Child Care) program?

      No, we are not enrolled in the program. As a fully accredited Montessori school through the CCMA, Dearcroft provides a premier learning environment and robust academic curriculum. While our Toddler and Casa programs are considered childcare and licensed through the Ministry, a Montessori program provides a specialized approach to learning in a responsive, prepared and adaptive environment delivered by extensively trained Montessori staff.

      At Dearcroft, we provide a comprehensive and individualized curriculum, featuring a fully academic, developmentally appropriate programs within a full school community setting. Our level of programming encompasses all aspects of development in a “whole child approach".


        PERFECT place to set the base for your child

        The toddler’s class at Dearcroft Montessori is the PERFECT place to set the base for your child to build up. We were so lucky our daughter Kaya had the chance to be part of the lovely welcoming environment there. The effective way of teaching was clearly reflected on how Kaya advanced her way of independence. We have found at Dearcroft our extended family, a safe environment that would nurture the development and learning of our children. Thanks to all the wonderful teachers and staff!

        Hiba Nashef and Rani Chamie

        Grateful for the future of our children

        You educated my kids (and me) in such a wonderful way and guided my daughter to veterinarian school and my son to a creative destiny. I’m grateful for what Dearcroft/West Wind has done for the future of our children.

        – Dearcroft Alumni Parent 

        A Magical School

        Gord Phippen – you and your family created a magical school that educated both our children. It taught them to be kind. To be wise. To inquire and enquire. For that gift, I am eternally grateful.

        – Dearcroft Parent