Upper Elementary Head Teacher (Maternity Leave)

Washington Montessori School 

Job posting: Upper Elementary Head Teacher, Grades 4-5 (Maternity Leave) - March - June 2026

Washington Montessori School creates an inclusive and joyful environment, supported by a deeply rooted community of families and educators, where children embrace their individual and collective potential and prepare to live with integrity in a changing world. 

Our values: Independence. Belonging. Purpose.

Washington Montessori School (WMS) seeks an experienced Upper Elementary teacher to join our program for the spring of 2026 (March, 2026 - June 17, 2026) Montessori teacher credentials and experience are strongly preferred. Located in Litchfield County, CT, WMS is less than an hour from Great Barrington, MA, less than two hours from NYC, and an easy day trip to Boston.

Founded in 1965, Washington Montessori School exists to educate children and to teach and nurture the skills necessary for success in a changing world through a foundation of Montessori philosophy and principles and best educational practices. WMS also upholds the highest standards of independent school education as articulated in the Standards of the Connecticut Association of Independent Schools, Principles of Good Practice of the National Association of Independent Schools, and the American Montessori Society’s Philosophy and Practice and Code of Ethics.

Successful candidates will join a dynamic, supportive, and forward-thinking teaching community of over 50 adults serving 268 students from 18 months through 8th grade. 

Responsibilities:

• Carry out the documented plans of the Head Teacher on leave.
• Create an organized, warm Montessori environment for children in grades 4 and 5
• Work in partnership with parents and colleagues
• Work in partnership with an associate teacher.

Requirements: 

• Elementary II Montessori certification and experience with grades 4-5 
• At least 3 years of head teaching experience  
• A Bachelor’s degree
• Excellent references
• Strong verbal and written communication skills
• The desire and ability to work collaboratively with parents and colleagues
• Excellent organizational skills and attention to detail
• The physical ability to care for a classroom of small children 
• Individuals with diverse backgrounds and experiences are strongly encouraged to apply

To Apply: 

Please submit a resume and a cover letter describing the alignment of your skills with the position described above to Interim Head of School Kerry Dorton [email protected], and Director of Education [email protected], or mail to 

Melissa Hay, Director of Education

Washington Montessori School, 

240 Litchfield Turnpike, New Preston, CT 06777