Mathematics is a critical part of academic preparation of the middle school child, or, as Dr. Maria Montessori would refer to them, children in the third plane of development. Montessori educators are sincere in their endeavors not only to prepare young students for further studies of math and the application of math in their world and careers, but also to build their confidence and ignite interest in the beauty of mathematics. In this article, the author describes the results of her study on Math tracks in Montessori middle schools and what serves the child best in preparation for high school. Three groups were surveyed: (1) alumni of Princeton Montessori Middle School; (2) math department heads of the high schools Princeton Montessori Middle School students attend most; and (3) other middle school program heads (Montessori, private, and public). (Contains 6 online resources.)