My (Westminster School's) golf team plays out of Simsbury Farms GC, a mediocre muni that is no fun at all trudging the mud in the early spring (worst drainage I've ever seen). I really wish our A.D. and coach could figure out a way to make it so we could play out of Wintonbury Hills. It's only a couple minutes further away from school than Simsbury Farms, and probably not-too-much more expensive.
A couple teams in our league play at really nice courses. Taft owns part of the land of Watertown CC, which is a nice old course, and Hotchkiss had its own course, originally done by Seth Raynor (before new construction). Canterbury school alternates between Lake Waramaug CC, a great little nine holer in New Preston, CT, and Fazio's Bull's Bridge CC. Salisbury plays at turn-of-the-century Sharon CC, which has some of the smallest greens I've ever seen, and is great fun. The Berkshire School plays at Wyantenuck CC, which I've heard is quite nice.
My Pre-Calculus teacher used to coach JV golf at Robert Louis Stevenson. He's played Pebble, Poppy Hills, and Spyglass dozens of times each. Why he decided to come to CT is a bit of a mystery.