I “second” what @Temperantia stated - We have friends who live close to Hotchkiss. It’s wonderful and there are some fun places to dine out in Millerton, NY (just a 10 minute drive or so from school). Great pizza place, diner, cozy restaurant, take-out place, book store, bike trail. Also, we love the White Hart Inn @ for dining and for overnight stays Salisbury. Great golf at school and nearby, also! Plus, you are not too far from Sheffield, MA & Great Barrington areas.