New Canaan Country School, a Pre-K through Grade 9 co-ed, independent day school, serves approximately 570 students from diverse backgrounds living in 18 different towns/cities across Fairfield and Westchester counties. Our mission is to create an active, joyful learning environment where children are challenged to think deeply, question confidently, and act generously so that they may lead lives of impact and purpose. We believe that childhood is in itself an integral part of life to be lived fully and happily. A talented and devoted faculty engages our students in developmentally appropriate ways, delivering a challenging curriculum that builds intellectual skills and fosters creative and critical thinking.

The Apprentice Teacher Training Program at New Canaan Country School provides "on the job" training for individuals interested in becoming elementary and middle school teachers. Classroom placements range from kindergarten to sixth grade. Each apprentice works directly alongside a lead teacher, and together, they provide instruction to students in language arts, mathematics, and social studies. For those interested in sports, apprentices have opportunities to coach in the school’s interscholastic athletic program. On Wednesday afternoons, apprentices attend faculty meetings and participate in seminars that address a variety of topics in teaching and education.

This program is uniquely designed to give beginning teachers the experience and training they need to go out and lead classrooms of their own. Country School is a leader in teacher training with nearly 1,000 apprentices coming through the program since 1952. We welcome anyone thinking of pursuing a career in education to apply.

The Apprentice Teacher Training Program is total immersion into the teaching profession. The school provides a stipend of $30,000 to its first-year apprentices (with an increase for each following year of service), and housing is available for a modest fee. There is some financial support for apprentices who wish to begin graduate work. Through this comprehensive work experience, apprentices who complete the program gain a unique stepping-stone for a career in teaching. Upon completion of the Apprentice Teacher Training Program, most apprentices either apply for lead teacher positions or enter graduate school. This is a full-time position for the 2026-2027 school year.

Apprentice Teacher placements are available in:

• Early Childhood Division: Kindergarten
• Lower School Division: Grades 1-4
• Middle School Division: Grades 5-6

Responsibilities

• Work collaboratively with Lead Teacher in all aspects of classroom life including:
• Supporting and modeling positive discipline
• Preparing and planning curriculum materials
• Evaluating student work and communication with families
• Gradually increasing responsibility for teaching students in small and whole groups in all subject areas
• Divisional supervisory responsibilities including:
• -- Early Childhood & Lower School: recess supervision, lunch table management, escorting of students to other classrooms, bus coordination
• -- Middle School: recess supervision, lunch table management, bus coordination, assistant or lead coaching
• Attend faculty meetings and Professional Development seminars
• Be available Monday-Friday 7:45-4:15 on school days and for some evening events throughout the year.

• Bachelor’s degree from an accredited college or university
• Successful experience working with children
• Strong verbal and written communication skills
• Demonstrated interest in teaching
• Understanding of technology and its applications in schools
• Preferred, but not required:
• --Interest in coaching or assisting with After School activities
• --College or university GPA of 3.0 or above preferred
• --Experience with Responsive Classroom approach

Desired Qualities

• Self-reflectiveness
• Collaboration with colleagues
• Communication to multiple audiences
• Comfort with and adaptability in fast-paced environments
• Strong organizational skills and attention to detail
• Inexhaustible energy
• A sense of humor
• A commitment to equity, inclusion, and fostering of a culture of belonging for our community
• Willingness to be challenged

About New Canaan Country School

New Canaan Country School is a co-ed, independent day school for students in Pre-K (ages 3 & 4) through Grade 9 living in Fairfield and Westchester Counties. Located in New Canaan, CT, and serving 570 students, our mission is to guide students to reach their intellectual, creative, moral, and physical potential. A talented and devoted faculty engages our students in developmentally appropriate ways, delivering a challenging curriculum that builds intellectual skills and fosters creative and critical thinking. We lead by example and challenge students to fulfill their potential, find their path, and follow their passions whether in the classroom, on the playing fields, on the stage, or serving the community.

Connections working at New Canaan Country School