Welcome to Headwater Hills Montessori School

Who are we?

HHMS is an independent, non-denominational, CCMA-accredited Montessori school for children ages 3 to Grade 8, located in Caledon, just south of Orangeville. Set on several acres of naturalized forest, meadow, and nature trails, our school offers a learning environment deeply connected to nature. Since 2010, we have fostered a caring, supportive, and stimulating community where every child is seen and celebrated, and where children grow into self-confident, independent, and joyful learners.

Our Mission

Headwater Hills Montessori School aims to provide an environment where children can be who they are and become who they are meant to be. Our commitment is to create a kind, calm, joyful, and engaging community that supports each child in becoming their very best self.

We value and nurture strong connections with self, community, and nature, recognizing these as the foundation for self-love, care for others, and respect for the earth and all its inhabitants. We strive to provide an open, welcoming, inclusive, and safe environment for all, and we actively celebrate diversity in all its forms. We believe that embracing diversity enriches our community and lays an important foundation for compassion, justice, dignity, and a sense of worth.

We hold a vision for our students to grow into engaged and thoughtful citizens of the world, bringing forward their unique spark to contribute meaningfully and positively to the world around them.

Why choose HHMS for your child?

Choosing a school is one of the most important decisions a family makes. At Headwater Hills Montessori School, we offer an authentic Montessori education within a caring, connected community where children feel safe, supported, and inspired to grow.

CCMA / Montessori Canada Accredited
We are a Montessori Canada (CCMA) accredited Montessori school serving children from age three through Grade 8. Montessori Canada accreditation is the strongest assurance of an authentic Montessori education, reflecting high standards in teacher training, curriculum, and classroom practice. Learn more about Montessori Canada/CCMA.

A Caring, Nurturing, and Safe Learning Environment
Children learn best when they feel safe and experience a strong sense of belonging. At Headwater Hills, we intentionally cultivate an atmosphere of acceptance, respect, and collaboration. The result is a positive, supportive, and kind learning community where children feel valued and confident to take risks in their learning.

Experienced and Highly Qualified Teachers
Our teachers bring many years of experience and are highly qualified, including MACTE-certified Montessori training. They understand how children learn and grow, and they know how to engage, challenge, and support each child while bringing out their individual strengths.

A Diverse, Welcoming, and Inclusive Community
Headwater Hills is a diverse and inclusive community that truly feels like family. We actively celebrate the rich diversity of our families and invite parents to share their culture, heritage, traditions, interests, and skills as meaningful enrichments to our program. Families are encouraged to be involved and connected members of our school community.

Individual Attention and Personalized Learning
No two children learn in the same way. Our personalized approach is tailored to each student’s interests, strengths, learning style, and areas of challenge. This approach increases engagement and achievement while supporting each child’s growth. Students are optimally challenged — those ready to advance may move well beyond grade level, while those who need extra support receive the one-on-one guidance necessary to succeed. Every child is seen, supported, and celebrated for who they are.

Building Confidence and Self-Expression
Through the arts, music, movement, drama, and collaborative work, students develop confidence, independence, and a strong sense of self. Leadership, initiative, and mentorship are woven into daily school life, and community events such as drama productions, Literary Tea, Celebration of Light, and Spring Soirée offer supportive opportunities for children to share their learning and creative expression.

Forest School, Nature, and Outdoor Learning
Connecting children to the natural world is a core value at Headwater Hills. Our weekly Forest Friday half-day nature immersion program is an integral part of the curriculum for Casa and Elementary students. In addition, students engage in gardening, nature walks on our trails, tree planting, outdoor education field trips, farm visits, and Middle School camping trips. Through these experiences, children develop resilience, confidence, collaboration skills, and a deep appreciation for the natural world.

Social and Emotional Development
From the age of three, we intentionally support children’s social and emotional growth through daily experiences. Grace and courtesy, conflict-resolution skills, kindness, and compassion are modelled and practiced throughout the day. Students develop communication and relationship skills, leadership, mindfulness, and self-awareness as part of the curriculum.

French for All Ages
From the age of three, all students are introduced to spoken and written French. Learning takes place through songs, games, stories, and drama, making French accessible, engaging, and enjoyable for children of all ages.

Physical Education and Movement
Our Elementary and Middle School physical education program is diverse and taught by specialists from the community. Students participate in a wide range of activities, including tennis, squash, pickleball, cross-country and downhill skiing, volleyball, basketball, track and field, soccer, dance, yoga, gymnastics, rowing, and more — supporting physical development, confidence, and a lifelong appreciation for movement.

We invite you to visit and experience how authentic Montessori education, time in nature, and a strong sense of belonging come together at Headwater Hills.

Our Montessori Programs

Our programs are uniquely designed for each developmental stage. Click on a program below to learn more about the way a Montessori education can benefit your child's growth and positive development at each level: