as a boy, reynolds attended miss gaylord's boarding school in catskill, new york. he later attended the albany academy in albany and graduated from st. paul's school in concord, new hampshire in 1886. he entered williams college in williamstown, massachusetts in the fall, where he became involved in the sigma phi fraternity. reynolds was an avid photographer while in college, documenting architectural details on campus as well as collecting portraits of many of his classmates. reynolds decided to pursue architecture and enrolled in the architectural program at columbia university's school of mines after graduating from williams in 1890. reynolds graduated from columbia in 1893. his thesis, "housing of the poor in american cities", won him a prize from the american economic society and earned him an honorary master of arts degree from williams college. it is still cited in scholarly work to this day.