Oakville’s Original Montessori School

Celebrating 50+ Years of Leadership and Innovation

Two locations to serve you:
Lakeshore campus and North Oakville campus


At Dearcroft Montessori School / West Wind your child will experience…

  • Bright, Spacious, Naturally Lit Classrooms
  • Beautifully Wooded, Historic Estate Property
  • Fully Qualified, Experienced Montessori Teachers
  • Optimal Class Sizes & Teacher/Student Ratio
  • Enriched French and Music Programs
  • Advanced Computer Technology / Smartboard
  • Great Lakes / Canadian Heritage River Curriculum
  • After School Activities and Clubs
  • Travel Opportunities
  • Incredible Outdoor Education
  • Extensive Phys. Ed. Program & Annual Winter Trip
  • Indoor and Outdoor Performing Art Stages
  • Model United Nations Program / NY City
  • Lunch Program & Before/After School Care
  • Transportation available

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We offer small class sizes


We have an energetic, multi-disciplined team delivering an enriched curriculum.

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

Programs and Services

In addition, our school offers the following programs and services:

  • Before and After School Care
  • Hot Meal Plan Option
  • Transportation services through Kids Limo
  • A variety of extracurricular clubs and programs including Arts Club (Drama), Chess Club, Bricks 4 Kidz, PSAA Athletics
  • Many community events such as the Fall Festival, Christmas Concert, Christmas Luncheon, Heritage Day, Art Show, Science Day/Fair, Arts Club Show, and Year End BBQ
  • French Program