All posts by Dearcroft Montessori

Testimonial Video

On behalf of our amazing Dearcroft Montessori community…. present families and those from our past five decades of operation who have also helped build the very foundation of our success, we are most humbled to share the stories  profiled in this testimonial video.  They reflect a tremendous shared commitment and love for the unique culture of our school. The very special family we are all a part of. Thanks to those who have made this wonderful video possible and to all of you for being a part of our remarkable Dearcroft journey… since 1968.


Elementary and Junior High Learn Remotely January 5th -8th 2021

Dear Parents,

We hope you are having a wonderful winter break and are enjoying some time outdoors.  As we prepare for the start of 2021, and our second term, we wanted to reach out with some reminders.

As you know, there are currently a range of time-limited public health actions to help curb the spread of COVID-19, which also includes at home learning from January 5-8, 2021.  At this time, our Elementary and Junior High teachers have prepared to transition to online learning for this coming week.

Second Term begins In-person learning for Toddler and Casa students

Dear Toddler and Casa parents,


We hope you have had a wonderful winter break and are enjoyed some outdoor time.  As we are  prepared to welcome back our Toddler and Casa students on campus for the start of 2021, and our second term.
Our first day of school is Tuesday, January 5th.  While there are currently a range of time-limited public health actions to help curb the spread of COVID-19, child care centres will remain open during this time.  Therefore, during the period of January 5-8, 2021, while our elementary levels are operating virtually, our Toddler and Casa programs will return to in-person learning.  However, please note before and after school programs will be closed.

West Wind Junior High is raising funds to support education in Wabauskang First Nation through SchoolBOX North

Hello parents and students,

We are Hugh and Holly from the West Wind Junior High classroom. This term our classroom has been studying First Nations. Moreover, we just finished an eight-week independent study project on the Residential School System.

Residential Schools have had a lasting and multigenerational impact on First Nations all across Canada. Additionally, many modern First Nations currently lack access to education. For this reason, we are organizing an Orange Shirt Day fundraiser to help raise awareness of the lasting impacts of residential schools, as well as helping to improve the access to education for a Northern First Nation community.

We ask on Tuesday, December 15 every student wear an Orange Shirt to spread awareness of the effects residential schools have had on First Nations. Additionally, we are asking for any donations, small or large, from the Dearcroft community. All of the proceeds from the event will go to the charity SchoolBox North, which is helping the Wabauskang First Nation community improve their access to education. This community located in Dryden Ontario is currently lacking a classroom, and the children have to drive an hour to get to school and an hour back each day. We are trying to buy them the necessities of a classroom such as desks, chairs and computers. The donations would greatly benefit this community, and we thank you in advance for your support.

If you are able to, we ask you donate to SchoolBox North through the link below:

For more information about please check out this blog series trying to dispel myths and educate people about indigenous issues.

Q & A Dearcroft and West Wind Montessori School

questions answers Dearcroft Montessori, Q&A, Dearcroft Montessori, Montessori school, private 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, 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 countrie’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 their post-secondary education opportunities and career paths beyond.


How did Dearcroft and West Wind Montessori school respond to the mandated closure last Spring?

Last year, when Dearcroft pivoted to online learning in response to the Covid-19 pandemic school closure, we found a new opportunity to continue providing the highest possible level of education to our students.  Dearcroft was able to transition  quickly to our online learning portal in just a few weeks partnering with Desire 2 Learn (, a top rated virtual education platform  and launched our portal.  This allowed our students to continue learning remotely while maintaining their grade levels and gaining full access to our curriculum as they finished the school year.

This truly outstanding effort was extremely well received and went well above what many students experienced in our province.  Dearcroft teachers provided excellent online learning for all of our students and we received tremendously positive feedback from our parents in this regard.

In fact, Montessori students flourish with online learning as they are already able to be independent, self-directed learners through a guided curriculum.  Montessori students develop a responsibility for their own work, something most students do not learn effectively until their senior years  of high school of even their post secondary education.


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.