Heralds announced the guests as they arrived at the dinner. Students, faculty, and staff all dressed up in elaborate 16th century costumes for the occasion. Members of the student government, seated at a separate table, played the part of nobles, and entertainment was provided by jesters and carolers. After dinner, a short play telling the story of St. George and the Dragon was performed, and carolers sang. During her time at Simmons, Catherine participated as one of the carolers.

The last Olde English Dinner at Simmons took place in 1969.