Town Plot, at the top of the hill, was the original place of settlement in Waterbury in the 17th century before the permanent town was laid out on the east side of the river. The continued occupation of the high ridge can be seen in the 19th century farm houses that survive along Highland Avenue.
In the early decades of the 20th century, Town Plot attracted new homeowners seeking more open space than the densely settled, older neighborhoods of Brooklyn and the South End could offer. Civic improvements in the area, including the development of Chase Park in 1911, the construction of Chase Parkway in the 1920s, and the construction of St. Margaret's school in 1927, brought greater public attention and transportation services to the neighborhood.
Many of the new homeowners were Italian families building single family homes, often in proximity to other family members. Many of the homes were built by the owners themselves, with the help of family and friends, with extensive vegetable gardens nearby. The construction of the church and school of Our Lady of Mt. Carmel, in the 1940s and '50s, and its related festivals and activities added to the attraction and vitality of the neighborhood, and served as a center for a close-knit Italian community. Nearly a third of the residents were Italian natives or first generation in Waterbury in 1970.