Organized intercollegiate fleet racing began in 1928 between just a few schools in Eight-Metres for the Oliver Hay Trophy, now known as the McMillan Cup.

There was also a major sailing event between Princeton and Dartmouth in 1934, but details of its format are not recorded.

[10] In the fall of 1937, 19 colleges took part in another ICYRA dinghy regatta at the MIT Pavilion.

[11] The Morss Trophy was also first awarded in 1937, being won by MIT[12][13] Following World War II, collegiate sailing spread across the U.S. and parts of Canada, with ICYRA membership rapidly growing to modern numbers.

Each conference conducts local and intersectional regattas and holds district championships in both the fall and the spring.

The Hall of Fame is located in the Robert Crown Sailing Center[19] at the United States Naval Academy in Annapolis, Maryland.

There are several awards that are bestowed upon collegiate sailors at the end of every full racing season: ICSA seeks to promote the sport of sailing throughout North America and encourage participation in the sport among young people.

Although both varsity and club teams compete fiercely to qualify for district championships and nationals, the overall goal is to promote sailing and have fun on the water.