J.W. Livingston, a well-known teacher in southwestern Wisconsin, taught at Dodgeville between 1877 and 1890. A new high school that "ranked with the best in the state" was built in 1881. Four students received their diplomas in 1883, were the first to be awarded in Dodgeville. $7000 was spent on improvements in 1891, providing a kindergarten, better equipment, and furnishings for the school. A new high school was built next to the old one in 1906. This building eventually became the middle school and was demolished in 2004. A new high school was built in 1939 to provide more space for students. The current high school building was built in 1962, and the current middle school building in 1994. Ridgeway High School and Dodgeville High School combined into a single entity in Dodgeville in 1963.