Located in the foothills of the Berkshire Mountains, the Hotchkiss Golf Course circles the campus of the school, which is located on the top of a hill overlooking the village of Lakeville, Connecticut. In 1924, prominent golf course architect Seth Raynor designed the course, which still retains some of the best examples of his work in New England.

Raynor's course so enraptured Charles Banks, a Hotchkiss English teacher, that he formed a close friendship with Raynor, developed his own passion for golf course design, and ultimately joined Raynor in a partnership. They worked closely together until 1926 when Raynor died at the age of 42. After Raynor's death, Banks completed over 30 unfinished Raynor courses, and returned to Hotchkiss in the 1930s to reconfigure several holes.

Playing at Hotchkiss is like playing in another era. The combination of a beautifully landscaped campus replete with stately brick buildings and an old golf atmosphere makes for a unique golfing experience. At just over 3,000 yards and a par of 35, the nine-hole course provides challenging play.