In May 2006, American Idol runner-up Clay Aiken made a surprise visit to the school in gratitude for its UNICEF contributions of $14,000 that year.

In twenty-four of those years[clarification needed] MMS' own geography bee champions have qualified for the statewide rounds and took the state championship in 1989, 2005, 2006, 2011, 2012, 2013, 2014, and 2018-representing Connecticut eight times at nationals.

[citation needed] On April 20, 2016, Middlesex was the chosen site for the National History Bee's Bridgeport Regional Finals.

Part of this curriculum includes the Google Expeditions AR program — a unique experience offered to select schools nationally to introduce Augmented Reality educational tools under development.

[6] The 1937 school building, a brick Colonial revival structure, sits on a 27.34-acre (110,600 m2)[7] site at 204 Hollow Tree Ridge Road.