Four Winds School in Gill, MA is seeking a full-time Humanities/ELA teacher to work with 10- to 14-year-old students in an independent learning environment.  

This is a temporary position: August 1st, 2022 – June 9th, 2023

Four Winds School is a small, independent middle school based on the one-room schoolhouse model. At Four Winds, students work at their own level and pace on self-assigned work. Learn more about our program on our website: 

Our ideal candidate:

  • Feels comfortable teaching middle school Humanities and ELA concepts. 
  • Has experience (and enjoys!) working with adolescents ages 10-14.
  • Has experience working with neurodivergent, gifted, and lgbtq+ students.
  • Is aligned with our policies around social emotional learning and social justice. For example, is current with politically correct language, accepting of all genders, anti-racist, and does not promote gender roles or discrimination of any kind.
  • Cares about alternative education and “meeting students where they are”.

Job responsibilities include

  • Planning for and teaching two one-hour humanities classes per week. The topic will be local history, including the indigenous perspective on European colonization. Two one-hour prep periods are built into the weekly schedule.
  • Assisting students with independent ELA assignments such as reading, vocabulary, and essay writing.
  • Leading a 45-minute “book club” every other Friday. 
  • Writing a “Biweekly Update” email to the parents every other week. 
  • Occasional after-school commitments, such as parent/teacher conferences, the beginning of the year family meet’n’greet, quarterly open houses, and graduation.

Salary and benefits: 

  • This position is full time (M-F 8:30-3:30 or 4:30) and pays a salary of $31,000. 
  • Full-time employees’ health insurance premiums are reimbursed or paid directly by the school, up to $500/month (does not include spouse or dependents).

To apply: please send a resumé and cover letter to and we will contact you regarding next steps. Please feel free to ask any questions! 

Note: We currently require masks, and all students and staff are required to be fully vaccinated against Covid-19. Our board’s covid committee will likely revisit our policies over the summer.