Maccheroni worked with Montessori throughout her professional life, and was a major contributor to the development of musical education in the Montessori method. The current study aimed to distinguish the characteristics of singing in the Montessori Method through an examination of documents written by Maccheroni. Our analysis revealed four main components of singing education in the Montessori method: 1) The use of singing as a daily activity; 2) The development of singing techniques; 3) Developing an understanding of the elements of music; and 4) Learning ways to express oneself through the development of artistry. Overall, our results revealed several distinctive features of Maccheroni’s method of singing education, as a way of teaching children to express themselves through the unique worldview of their own music.