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- The first school in the Town of Middleton was probably built by J.D. Sanford in 1847. The log building, costing $144 was likely constructed in or near Section 27, along Mineral Point Road.
- The first school house, in what is now the city of Middleton, was believed to be located on or near the site of the St. Bernard Parish Cemetery on Branch Street.
- In 1872, Middleton opened a brick and stone elementary school near the Quarry on Terrace Avenue. Some sources indicate it burned in 1884. The building was replaced by a two-story frame building on the same location that continued to be used as an elementary school until the new Elm Lawn School (between South and Hubbard Avenues) opened its doors in 1913. Later, the frame building served as the Masonic Temple before it was moved to Hubbard Avenue where it became the new Village Hall.
- In 1879, Middleton opened the doors to its first High School. The brick structure, built for $1,000, still stands at the corner of Terrace Ave. and N. High Point Road. Sixteen applicants passed an entrance exam and were admitted to the first session which lasted 3 months. The first teacher, Mr. C.E. Buell, was paid $200.
- The old Pheasant Branch School, now the VFW Post on Century Avenue, was built in 1896 and served as the second graded school in the area until the 1950s when it was acquired by the local Veterans of Foreign Wars.
- A second High School, a 2-story brick building, was built in 1903 at the corner of Middleton and Franklin Streets. This served the community until 1918 when a third school was built on a 3-acre North Avenue tract. After serving Middleton students for about 15 years, the former high school (on Middleton and Franklin streets) became home to the Masonic Temple.