Happy Hollow School was founded in 1956 by Gloria Kingsbury Malone.  Truly an innovator in the field of early education, Mrs. Kingsbury, as she was known to all her students and families, purchased land on Oaks Road in 1954 and built her home and her beloved school.  In 1956, Happy Hollow School opened its doors as a kindergarten and nursery school.

From our small beginning 60 years ago, Happy Hollow School’s philosophy has always been to provide a warm, nurturing environment, staffed by caring professionals, where children are encouraged and stimulated. The natural curiosity and uniqueness of each child is encouraged and respected. Every child’s first steps away from home and parents is welcomed into a learning environment created and organized to develop each child’s potential--- physically, emotionally, intellectually, and socially.  The entire building is now used to create a bright and stimulating learning environment that includes a library and an indoor gym area.


Our Goal for our Students

Happy Hollow School's goal is to provide each individual child with a warm and understanding environment making each child's first school experience happy, encouraging and confidence-building.

My son is going to Pre-school full-time here and LOVES it! I love the teachers and love the environment.
— Eleanor, Parent

HHS at a Glance

  • Providing programs for children aged 15 months to 6 years

  • Excellent student to teacher ratios allowing for small and large group and one-on-one interactions

  • Two, Three, Four and Five Day programs

  • Half and Full Day Programs available

  • Toddler Program (15 to 33 months)

  • Preschool Program (2.9 to 4 years)

  • Prekindergarten Program (4 to 6 years)

  • Music and Movement Program

  • Early Drop-off and After-school Extended Day Program offered

  • Active and vibrant parent association provides enrichment programs and support to families

  • Fully licensed by the MA Department of Early Education and Care

  • NAEYC Accredited


Our Teachers

Our nurturing and dedicated staff has devoted their careers to early childhood education.

  • Our teachers hold college degrees in early childhood education or a related field.

  • Teachers are certified by the MA Department of Early Education and Care

  • Annually certified in CPR and First Aid