Weimer K. Hicks Achievement Award: This award is given to the senior, who in the estimation of the faculty, has shown marked progress in all phases of Wayland life.

Alumni Memorial Service Awards for Service: Presented by the Wayland Alumni Association, this honor is granted irrespective of class, scholastic, or athletic ability to that young man and to that young woman who have, in the opinion of the faculty, made valuable contributions to Wayland through unselfish service and generous giving of their time and talents. 

Board of Trustees Awards: Awarded to the graduates who have demonstrated an interest in Wayland and whose performances have helped to create loyalty and dedication toward the goals and objectives embraced in a Wayland education. Their contributions to dormitory living, extracurricular activities, and all other phases of campus life are considered in the selection process.

Glen and Ella Dye Award:  In 1979, Wayland Academy initiated the Glen and Ella Dye Award in memory of two former alumni, benefactors, and trustees. The award is given to that student, irrespective of class, whose behavior is exemplary in religious earnestness and moral sensitivity.

James P. Freeman President’s Award: In 1995, Ralph Robinson `64, established an award in memory of one of his Wayland classmates—the James P. Freeman President’s Award. This award is presented annually by the members of the senior class to the individual who exemplifies the characteristics of Jim Freeman, in their relationships with others. Jim Freeman, class of 1964, was recognized as a nonjudgmental friend to all groups, an individual who was open and available to anyone and who gave of himself to others without expectation of gain. Jim demonstrated loving kindness equally, to everyone with whom he interacted.

Head of School's Award: This special award is given on those occasions when students deserve special recognition for long-term contributions to the student body and the community of Wayland Academy. 

Kit Mayer Sports Cup: This primarily an athletic award based on the following qualifications:

• the recipient must be a member of the girls' varsity club in good standing;
• have earned a varsity letter in at least one sport;
• have satisfactory scholastic standing;
• have displayed good citizenship and lofty ideals of sportsmanlike conduct in various undertakings.

Wiseheart Cup: This award goes to the young man who has best fulfilled the following standards:

• won his letter in one sport and has taken part in two others;
• has a satisfactory scholastic standing;
• is outstanding in leadership in all forms of activity;
• and whose sportsmanship is unquestioned.

Laura A. Mac Donald Award: This award is the most significant honor bestowed upon a young woman at Wayland Academy. It is given to the senior, whose actions and demeanor bespeak self-respect, courteous consideration for others, and loyalty to the academy and its traditions. She must be a leader in scholarship and other school activities.

Edwin Putnam Brown Award: This is the most significant honor bestowed upon a young man at Wayland Academy. It is given to the senior who, with a sense of social responsibility and with fine school loyalty, has shown the highest type of leadership.