Montessori/Westwind Jr. High

Your Natural Choice Since 1968

Toddler to Grade 8

Commitment to providing an exceptional education.

News, Videos & Photos

View the latest news, videos, & photos from our events.

Find out more

Directions, phone numbers and emails, get in touch.


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. With a low student-to-teacher ratio, our staff enjoys ideal conditions for helping our students to achieve their personal and academic goals. 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.

Since 1968, Dearcroft has provided inspiration, opportunity and educational challenge within a nurturing, supportive environment, promoting maximum growth and development.

Operating for nearly 50 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 Temagami, Algonquin Park and Ottawa/Quebec City. For over 15 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, as well as Smartboard and Harkness table instruction on our campus, providing globally inspired curriculum in optimally sized classroom environments.

View our websites today and make an appointment to visit us. We invite you to discover the exciting educational opportunities at Dearcroft . . . Oakville’s original Montessori school.

Guiding - Inspiring - Advancing

Latest News and Events from Dearcroft Montessori

Dearcroft’s Heritage Day Success

Dearcroft Montessori's Heritage Day was a great success! After presentations, a poem and a song, students sat down to enjoy a lovely lunch, with delicious food from all over the world. What a wonderful celebration and how fortunate we are, to be living in Canada,...

Dearcroft Montessori’s Model UN Team Takes NYC

Dearcroft Montessori students apart of their Model United Nations team had the opportunity to take part in a Model UN Conference in New York City. What a great experience!

Dearcroft Remembers Rob Stewart

Despite our profound sadness in joining countless others around the globe in mourning the loss of our dear friend Rob Stewart... we are overwhelmed with gratitude for the gift of his extraordinary life. Thank you Rob for teaching us all the importance of loyalty,...

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 School & West Wind Montessori Jr. High

1167 Lakeshore Road East, Oakville, Ontario L6J 1L3

(905) 844-2114



Admissions Contact:

Catherine DeBorba

Tel: (905) 844-2114

Email: info@dearcroft-montessori.com

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

Don't Be Shy

If we didn’t answer all of your questions, feel free to view our college website.