Directed Free Choice programming has been at the heart of Windsor Mountain since 1961. This program mainstay, in which campers choose their own own activities with the help of their counselor, is central to a great summer experience.

Every three days, a variety of classes are offered for each of the four periods of the day. Counselors help each camper choose a combination of fun, short–term activities, as well as long–term projects like theatre and dance productions, a competitive inter-camp soccer game, a rock climbing trip, progressive tennis lessons, or the completion of a large permanent sculpture. As campers develop specific skills and interests, they are welcome to apprentice with a counselor.