In 2006, Todd Covert, Head of School, and Meagan Ledendecker, Director of Education, established Berkshire Montessori, LLC. Known as The Montessori School of the Berkshires, the school first took shape after Meagan and Todd met with a group of parents interested in Montessori education. This initial Parent Advisory Group provided the guidance, feedback, and support necessary for those initial formative steps.

Prior to opening the school doors, Meagan led a series of informational sessions to help the community learn more about Montessori education. Then in the Fall of 2006, the school opened with 24 students and three Montessori trained teachers. 

Now in its fifth year, the school is a non-profit 501(c)(3) entity, Berkshire Montessori School, Inc., with Toddler, Children's House, Elementary, and Adolescent programs. In 2009 the school purchased 40 acres of land in Lenox Dale and now celebrates one year at the new campus as one of the few LEED (Leadership in Energy and Environmental Design) schools in the nation. The school currently enrolls 90 students and is supported by 12 staff. 

Montessori teacher training is provided by Montessori Educators International, a MACTE accredited program.  The school is an accredited private school through the Massachusetts Department of Education and the Massachusetts Department of Early Education and Care.