It was also believed to be an ideal setting for young adults to grow intellectually, artistically and socially, while living and learning with students from the region and around the world.

[3] A liberal arts curriculum meant to promote "engaged and active learning" forms the basis of High Mowing's academics.

Each school day begins, for each grade, with "Main lesson Block" – an integrative hour and 45 minute class that runs for between three and four weeks.

Examples of electives include Naturalist, Great Novels, French, Spanish, and German, Philosophy, Biology, Physics, Filmmaking and Digital Arts, Eurythmy, Drawing and Painting, Woodwork, and Pottery.

The Waldorf curriculum for each grade is developmentally-based, focusing on the central question that students typically encounter at that age.

The demographic breakdown of the 108 students enrolled for 2013–14 was:[1] Chapel, held on Sunday nights on campus, was originally a weekly spiritual/religious event begun by the school's founder, Mrs. Emmet.

Students returning from Thanksgiving Break attend school on Sunday afternoon to commemorate the beginning of the holiday season.

A sizable percentage of the student body participates in the short play, which is followed by the Snow Goose Party, an annual students-only event.

The festival has a number of built-in traditions including a skit by the "fools", a movement-based rendition of the carol "A Partridge in a Pear Tree" by seniors, the reading of a Christmas story from the Bible in as many languages as are spoken in the school community, the Yule Log, wassailing, and the presentation of the Christmas book, a compilation of artwork (generally holiday-themed) made of the contributions of all students.

These include a pottery sale, musical performances, cake walks, games and other entertainment for children, a grease pole with a twenty dollar bill at the top, a cow plop competition (in which the winner is the one onto whose pre-purchased field space an ushered-in cow first excretes fecal matter), and the Maypole Dance.

The Maypole is a tall wooden pole buried in the ground on the center green-space and is a metaphor for the fertility of spring.

The Spring Fairy typically sprinkles flower petals and other plant materials on audience members as well as Queen and King Winter.

High Mowing is a member of NEPSAC District Two and competes with other New England schools with boys'/girls' soccer in the fall, boys'/girls' basketball in the winter, and boys' baseball and girls' lacrosse in the spring.