The Reunion Chair Award is given to the alumna whose enthusiasm and spirit in encouraging her class to return to Oldfields for Alumnae Weekend has been exemplary. 

The Alumnae Cup is the highest award given by the Alumnae Association, in recognition of outstanding trusteeship, singular service to Oldfields, and a sterling example of alumnae involvement.

The Jane Isdale Schaefer '52 Trustee Prize is given in recognition of lifelong dedication to Oldfields and to its motto of "Courage, Unselfishness and Largeness of Heart", an ideal which Jane epitomizes. 

The Oldfields Money Pillow is awarded to the alumnae class with the highest percent of participation in annual giving to the Oldfields Fund, which raises unrestricted funds each year to support and enhance the day-to-day work of the School.

The Peggy Samson Harris ’36 Distinguished Service Award was created in her honor to be given to an alumna who is characterized by her loyal devotion and outstanding efforts on behalf of Oldfields.