The school's academic departments include English, Math, Science & Technology, Social Studies, World Languages, Health & Wellness, Studio Art/Music/Wood, and Drama.

[7] Despite the small size, there are numerous Advanced Placement courses offered including Spanish, French, Latin, Environmental Science, Physics, Calculus (AB and BC), Statistics, English, and Studio Art.

The LMMHS campus includes a library, wood shop, film developing studio, greenhouse, and the Duffin Theater.

[10][11] Among them are: A member of the Berkshire County League under the MIAA, Lenox sports teams are known as the Millionaires in recognition of the town's prominence as a summer colony for some of the country's wealthiest families during the Gilded Age of the late 1800s.

However, many students have expressed dismay with the "Millionaires" moniker, arguing that it promotes an elitist and revisionist version of the town's history.

Greylock High School in Williamstown for both boys and girls cross country running and skiing.

Fall sports include soccer, cross country running, volleyball, football, crew, and golf.

Stockbridge eventually chose to consolidate with Great Barrington, but Lenox and Lee have maintained their independent districts.