Yearling Winter Weekend is a special time set aside for the Yearlings and their guests. It comes quickly after the end of the military intercession. For this reason, it is a good idea for your cadet to make arrangements for a date over the winter break. Guest accommodations in local hotels should also be planned well in advance for the weekend. The highlight of Yearling Winter Weekend is a Saturday evening banquet and formal dance.

This is normally not a Parents Weekend, but for cadets and their dates. Cadets wear their full dress uniform and dates wear formal dresses, or for male guests suit and tie. Cadets often make it a full weekend, with an evening in New York City, and then still have time to show their dates around West Point, and get ready for the dinner in the mess hall, and dance which is held in Eisenhower Hall on Saturday evening.