Montessori/Westwind Jr. High

Your Natural Choice Since 1968

Preschool to Grade 8

Commitment to providing an exceptional education.

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Delivering Bold and Inspiring Curriculum for Over 55 Years

Dearcroft Montessori & West Wind Junior High

Dearcroft offers Montessori programs from Toddler to Grade 8. Located on a magnificently wooded, historic estate in Old Oakville, Dearcroft is situated just steps from beautiful lakeside parks. Our school is accredited by CCMA (Canadian Council of Montessori Administrators) and is staffed by qualified, experienced and highly motivated teachers. Within classically structured and fully equipped Montessori classrooms, immersed in a naturally inspired setting, our students experience an exciting, well balanced curriculum. In close cooperation, all members of our school community recognize the strength of an outstanding team and are appreciative of the opportunity to work together in such a creative and exciting learning environment.

Dearcroft Montessori provides inspiration, opportunity and educational challenge within a nurturing, supportive environment, promoting maximum growth and development.

Operating for over 55 years, Dearcroft is also home to the West Wind Montessori Junior High program. West Wind is Canada’s award-winning leader in elementary experiential education. We offer outdoor education, including a rotation of winter trips to destinations such as Camp Wanakita, Ottawa and Quebec City. For over 25 years, our unique Expedition Education program has taken groups of our students coast-to-coast, exploring spectacular world heritage sites and national parks in Canadian locations as diverse as the Yukon and Newfoundland. As much a neighborhood school, as a school with a national vision.

Dearcroft is a proven leader within our educational community. Extended learning opportunities also include MMUN (Montessori Model United Nations) conferences held at U.N headquarters in New York City. This opportunity provides a globally inspired curriculum within an optimally sized classroom environment.

Dearcroft Montessori School is excited to offer bold and inspiring Montessori education to more families in Oakville.

Dearcroft Montessori Trafalgar Campus

Founded in 1968, Dearcroft is Oakville’s original Montessori School. Now celebrating over 55 years, Dearcroft is excited to grow with the community and be a part of the town’s future core in Upper Oakville at Trafalgar and Dundas Crossing. Our experienced staff take great pride in offering a warm and engaging environment for students. We are pleased to offer new families our exceptional Montessori educational programs, where the curriculum is tailored to meet the needs of each student. Dearcroft offers programs for Toddler (18 months-3 years), Casa (2.5 years- 5 years), through to Elementary (Grades 1-6).

Dearcroft Montessori Rebecca Campus

Located within the Peter Gilgan Family YMCA of Oakville, our close-knit school community will offer bright and spacious naturally lit classrooms, with entrances to the playground from the classrooms. This space is designed for children to foster the development of gross-motor movement keeping in-line with Montessori best practices, all classrooms feature: multi-age environment, low student/teacher ratios, hands-on experiential learning, and individual and small group lessons. 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. We are committed to the students at our school and ensure that they feel happy and safe in an inclusive environment within a supportive matrix of care, encouragement, and challenge.

Guiding - Inspiring - Advancing

Videos from our Dearcroft Montessori YouTube channel

Contact and Directions

Are you interested in finding out more about our school? Come visit us during an Open House, or contact us, and we will be happy to give you a personal tour of our school.

Dearcroft Montessori & West Wind Junior High
Lakeshore Campus

Admissions Contact: Susanne Homer
1167 Lakeshore Road East, Oakville, ON L6J 1L3

Dearcroft Montessori Trafalgar Crossing
North Oakville Campus

Admissions Contact: Niki Rockliffe
297 Oak Walk Drive, Oakville, ON L6H 6Z3

Dearcroft Montessori Rebecca
YMCA Campus

Admissions Contact: Sarah Anderson
410 Rebecca Street, Oakville ON L6K 1 K7

What Our Parents Are Saying

Don’t just take it from us, let our parents do the talking!

The teachers are truly caring, gifted, talented and extraordinary. I love everything about the school; it became part of my family.
Claudia, Parent of Grade 8 Grad

I work in education and visit schools and teachers around the world and I can confidently say that Dearcroft is easily one of the top learning environments I’ve had the privilege of participating in. I am proud to put my 3 children in this school despite all the other great options available in Oakville.
Ken, Parent of Junior Elementary, Casa and Toddler students

It speaks volumes when your child is happy to go school each and every day and feels safe, listened to, and valued. I believe my daughter’s memories from this school will be with her forever.
Anita, Parent of Junior High student

The owners, teachers and staff at Dearcroft are wonderful, caring people. The Montessori method, which allows children the freedom to focus where they’re most interested, and return to what challenges them, is incredible. It’s amazing how children can flourish when properly supported. The gorgeous treed campus is a child’s wonderland.
Matt, Parent of Senior Elementary and Casa students

Dearcroft Montessori School – Your Natural Choice Since 1968

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