For more than half a century Charles "Tip" Schaefer officiated on gridirons up and down Fairfield County and beyond. Not only that, for more than 50 years, baseball players learning their craft in the southwestern part of the state came in contact with him as well. Considered one of the best athletes to ever come out of Westport, Schaefer was known as a top-notch baseball player. Once his playing days were over it was only natural that he attempt to stay in the games he loved. The best way to do that was to don the blue suit or the striped shirt. Those decisions resulted in a five decade love affair that lasted well into his 70s. Officiating at a time when semi-professional and industrial league teams were at the height of their popularity, "Tip" could be found on those gridirons and diamonds as well. Those games weren't easy to work. but players knew and respected Schaefer for his fairness and control of the game. A mentor, friend and confidant to many up and coming officials, he not only groomed those who would don the stripes so that they would be ready for varsity ball, he recruited many who would become the foundation of the Fairfield County Football Officials Association. So respected was he by members of the new FCFOA, he was elected its first president. He continued to teach and mentor new officials in the craft of officiating. When the Connecticut Football Officials Association was formed to represent the regional boards, Schaefer was a proponent of the idea of the single voice for football officials, and signed onto the idea immediately. Schaefer was the guiding light of the Fairfield board during its infancy. He helped mold the association and state board into the respected organizations they are today.