One of the most important buildings designed by McKim, Mead & White in Naugatuck is the High School on Hillside Avenue, constructed in 1905. Naugatuck industrialist and philanthropist John H. Whittemore wanted the school to have a prominent position on a hill overlooking Naugatuck Green and the many other structures that he had commissioned the firm to design. To adapt to the sloping site, the firm created a building in which each of its three floors has an entrance at ground level and each side is designed with its own distinct appearance. Based on Greek temples, the school is constructed in pink granite and pressed buff brick. A new High School was built on Rubber Avenue in 1959 and, although the original school’s interior was damaged by fire in the 1960s, it was painstakingly restored to become a junior high school, now called Hillside Middle School.

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Old Naugatuck High School (1905)
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4 thoughts on “Old Naugatuck High School (1905)

  • November 25, 2013 at 11:35 am
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    I believe that my great uncle, A. Milton Napier,working for McKim, Meade, and White, was appointed to supervise the construction of the high school photographed above. I believe A. Milton Napier made
    such an impression of Mr. Whittemore,, that he wo was hired to do other work for Mr. Whittemore, possibly leading up to Milton Napier
    establishing Tide Water Building Co. Are there records to support
    such an assumption?

  • August 25, 2022 at 8:16 pm
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    did this school used to be called Hillside School in the early 1900’s? or is there a school closeby that may have been standing during 1907 that was called Hillside school?

  • May 1, 2023 at 9:01 pm
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    From1905 to 1959, it was Naugatuck Hugh School. In 1959 it became Hillside Middle School. A second middle school was built in the 1970s. Eventually, as student population peaked and then declined, the two schools were consolidated in the newer City Hill Middle School. Currently the 1905 building is Hillside Intermediate School.
    The building has a place in Ripley’s Believe It Or Not, because of one unique feature. All three entry levels of the school are on the same street – Hillside Avenue.

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