Winter Sports


Basketball has two teams, varsity (predominantly seventh and eighth graders) and junior varsity (predominantly fifth and sixth). All practices and home games take place in the Bontecou Gymnasium. Opponents are again predominantly independent schools in the region. 



Volleyball comprises students in fifth through eighth grades. Practice and home games take place in the Bontecou Gymnasium. Our main opponent is Rumsey Hall, one of the few middle schools with a winter volleyball team. 



Squash is a more recent addition to the winter sports program and has proved very popular. We practice and play matches on courts at the Millbrook School. DDS is one of the few middle schools in the area to play squash, so our opponents are mostly high school recreational or “third” teams. We play against Indian Mountain, Millbrook, and Trinity Pawling. 


Ski Team

The ski program was added in the 2021-2022 school year! Dutchess Day’s ski team will practice three days a week at Catamount Mountain and will compete with a couple of local schools. 


For five Fridays in the winter term, kindergarten through eighth grade leaves campus mid-day Friday and goes either skiing at Catamount or skating at Millbrook School. Lessons are provided for both activities.