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The Colonial was formed in 1976 by schools Assabet Valley, Bay Path, Keefe Tech, Monty Tech, and Nashoba Valley. The creation of the conference was a way for Vocational Schools in Central Massachusetts to play each other in their own league.
In 1977, the league accepted their first new member in Worcester Tech (then Worcester Voke) who was already member of the Inter-High League. They stayed a part of the Inter-High while in the Colonial therefore allowing them to compete for two league titles. They did this up until at least 2011, where they became full members of the Colonial.[3] In 1979, Tri-County RVT joined having been founded only two years prior.[4] It was a short stint, however, and in 1984, Tri-County departed for the Mayflower League "to promote their athletics".[5]
By 1985, the predominantly female Fanning Trade School joined the league, competing only in women's sports. A lot of controversy followed some of the teams who were required by MIAA to allow the few boys who wanted to play sports to play on girls' teams.[6]
Fanning Trade only stuck around until the 1990-91 school year, as they would merge with Worcester Tech in the following year. New faces joined in the early 90's, those being Minuteman (who would straddle both the Colonial and Commonwealth leagues for around a decade, before becoming a full time Commonwealth member), and the first non-vocational school, Murdock. Murdock would end up leaving for the more prestigious Mid-Wach around 1995 to join other public schools. During the same time, Nashoba Valley Tech also left, heading to the Commonwealth Conference. Replacing them was Blackstone Valley Tech, who had been a part of the Dual Valley Conference since its inception.[7]
During the 2000-01 school year, Hudson Catholic left the Catholic Suburban League for the Colonial; this was due to certain schools dominating the league and travel time between schools being too great.[8] They would stay a part of the conference until they closed in 2009.
As the 2010s rolled around, Charter Schools began joining the league. Parker Charter was the first, around 2010,[9] and Abby Kelley Foster and AMSA would jump from the Worcester County Athletic Conference in 2015.[10] The league did not have any further changes until its ending in 2025.
Note: From 1972 to 2012, football state championships were separated by region, so there would be multiple champions from each division. From 1972 to 1977 and from 1997 to 2008, it was split between Eastern Mass and Central/Western Mass and there would be two champions in each division. From 1978 to 1996 and from 2009 to 2012 Central and Western Mass split so there would be three champions in each division. In 2013 everything was combined and therefore only allowed one state champion per division.
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