He attended the Massachusetts Institute of Technology, where he graduated in 1898 with a bachelor's degree in architecture.
He returned to Chicago to study under Daniel H. Burnham, one of the city's most prominent architects.
[1] Upon his return in 1905, Tallmadge decided to start his own architectural firm with fellow Burnham draftsman Vernon S. Watson.
Although Watson was the chief designer, Tallmadge became the face of the firm due to his commitment as a historian and teacher.
Tallmadge later focused on publishing books instead of articles, completing three works.