The earliest summer session was held in 1892, called "The Colorado Summer School of Science, Philosophy and Languages". It was a month long, and continued annually for four years, up to 1895. It was held at Colorado Springs although in collaboration with the Universities at Boulder and Denver, and was staffed partly by CC faculty - for instance, physics professor Florian Cajori taught in its first year - and partly by external teachers. The mathematics teacher in the 1895 session was Professor M A Bailey from the Kansas State Normal School, Emporia.

The idea of a summer session was revived in the 1920's, and continued for eight years from 1923 to 1930, under the direction of Guy Albright, who was also the mathematics (and astronomy) teacher for most of those years. His faculty colleague William Lovitt also taught mathematics at the summer session.

The summer session was revived again in 1935 (during the depression, President Davies' was seeking ways of supporting faculty salaries) and has proved a continued success since then. During the 1930's meetings of the Cowles Commission were held in connection with the summer school, attracting a large number of distinguished statisticians and economists.

The mathematics courses were initially taught by Charles Sisam, and over the years many Colorado College mathematicians have taught at the school: Martha Belschner taught in the 1930's, Margaret Hansman in the 1940's and 1950's, and Joseph Leech in the 1950's. During the 60's and 70's few mathematics courses were offered in the summer except for various offerings for students seeking teaching certification (often taught by Bernard Gundlach). Then from the mid 70's to the end of the century, summer offerings in mathematics bordered on the sporadic - perhaps a calculus course or two, maybe a introductory computer science course, and more often, reading courses for students seeking a masters degree in teaching. However, mathematicians in the department did contribute to a variety of innovative summer programs - TRIBES program, San Luis Valley program, and programs for practicing teachers. In the summer of 1999, Mike Siddoway experimented with an introductory level history of mathematics course.

John Watkins from the mathematics department taught in summer programs for many years before accepting the call to be Dean of the Summer Session starting in 1999. He maintained his connection to the mathematics department, continued to teach a course here and there, and then returned to the department in 2001.

Professor Watkins handed over the stewardship of the summer session to Jim Henderson, another long-time member of the Mathematics Department. Professor Henderson became Dean of the Summer Session as of September, 2001. During his previous sabbatical (in 1998-1999), he had trained under an American Council of Education Fellowship to learn the intricacies of college administration.