History Of Overlook
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 The Overlook District is Waterbury's finest grouping of early, 20th-century suburban, residential architecture. You'll find well-designed examples of Queen Anne, Colonial Revival, Tudor Revival, and Arts and Crafts styles in the area, but the district is historically significant because it represents the earliest planned, suburban, residential development in Waterbury.

    Located to the north of and up hill from the commercial center of Waterbury, the area was commonly called Overlook for its commanding view of the city. It was developed at the turn of the twentieth century by Cornelius Cables who actually referred to it as Columbia Boulevard, after the area's main street. Cables envisioned the area as home to many of Waterbury's middle class working population.

   
    Prior to Cables' 1897 subdivision of the area, the land was owned by many of the city's industrialists such as Israel Holmes, Frederick Kingsbury, and George H. Clowes as well as farmer John McDonald. Well situated to the north of the premier nineteenth century residential section, Hillside, the mostly vacant land, consisting of the rolling crest of a hill, provided an excellent location for residential development.

    Cables' overall plan actually encompassed three subdivisions: Columbian Heights, (Columbia Boulevard bounded to the east by Farmington Avenue and to the west by Clowes Terrace, to the north by Fleming Street and to the south by Cables Avenue); Highland Park (located to the northwest of Columbian Heights), and Cottage Park (located to the northwest of Columbian Heights). The neighborhoods of Overlook were designed with different pocketbooks in mind. In an age when greater numbers of workers than ever before could realize the dream of home ownership, Cables advertised Columbian Heights and Highland Park, with their larger lots as areas most appropriate for large single family homes, while the small lots of Cottage Park were marketed to those of more modest income

    Laid out with curving streets off a wide main tree-lined boulevard divided by a grassy median, Columbia Boulevard (or Columbian Heights) provided a country-like retreat for homeowners which was still quite convenient to their jobs downtown. Cornelius Cables' subdivision of this land reflected then-new planning theories and attitudes that find their roots in America's romance with nature. Overlook was situated far enough away from the city to possess rural amenities such as gardens and lawns, while being a convenient and affordable commute to the workplace. It was a combination of city and country; rather than being isolated on a large piece of property, the suburban houses were uniformly placed on rather regular lots and, like rowhouses, they complimented the other houses on the street.

    Underlying the creation of the grand boulevard and curving streets was the belief that nature could offer an exemplary form and produce a curative effect. As industrial cities such as Waterbury expanded as centers of production, they simultaneously deteriorated as places for human life and activity. In a nostalgic attempt to overcome this reduction in the quality of life, this leafy suburb was offered as a restorative, natural environment - a dwelling place between the urban experience and the social values of an ideal rural order.

    Cables quickly sold house lots to individuals, so that by 1925 90% of Overlook was built up. Overlook's residents included a cross section of Waterbury's middle to upper-middle class, including members of many families who had built prominent homes in the Hillside Historic District to the south. A variety of houses were available to both men of average means such as insurance dealer John Littlejohn (50 Columbia Boulevard) as well as Scovill executive Chauncy P. Goss (24 Cables Avenue).