In the late 1990s, Fairfield's existing middle schools, Tomlinson and Fairfield Woods, suffered from overcrowding due to the town's increasing student population. Following a public referendum, the town elected to open a third middle school. Roger Ludlowe Middle School opened in September 1998 at 785 Unquowa Road. This was the former home to Roger Ludlowe High School, which closed in 1987 to be consolidated with Andrew Warde High School, forming Fairfield High School.
As the student population increased and moved up through the Fairfield Public Schools, overcrowding in Fairfield High School necessitated the re-opening of Fairfield's second high school. The problem arose of where the new high school would be located. The Board of Education voted that the new Fairfield Ludlowe High School (FLHS) would re-occupy the Roger Ludlowe building, and a brand-new RLMS building would be erected adjacent. The new building opened in August 2003, complete with a new athletic field complex to be shared with the high school.