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Bennett had acquired a sound understanding of how to create and sustain the type of improved landscape sought by an increasing number of Chicagoans, especially members of the middle class, who attributed a particular social significance to such landscapes.
The attraction of the lots in the Highlands was their close proximity to downtown and the presence of fifty houses already constructed, offering firm evidence of an emerging residential neighborhood. However, even more appealing were the improved “home surroundings” of the Highlands: “[S]treet and sidewalk improvements in and paid for; no special assessments. Beautiful shade trees on all streets…Congenial and refined neighbors.”4 These physical and social features of the Highlands were among the central components of improved residential landscapes in late nineteenth- and early twentieth-century Chicago. Bennett also drew upon a combination of title deed restrictions and his membership in a local voluntary association to exclude large apartment buildings and saloons, two institutions considered antithetical to the middle-class vision of home. The conveyance of title to lots in the Highlands prohibited construction of “flat and apartment buildings,” while Bennett's position as a director of the Hyde Park Protective Association (HPPA) provided the means to influence campaigns preventing the incursion of saloons into the Highlands and adjacent territory, legally part of a local prohibition district.5 The improved character of the Highlands was further ensured through the activities of the Jackson Park Highlands Improvement Association (JPHIA). Coordinating local development while Bennett's “Highland Company” continued to build new houses and extend the subdivision, the JPHIA enlisted residents and the local alderman in their quest for “beautiful yards and parkways.” In addition to privately financing street lighting, telephone conduits, and tree planting, the association managed a zealous cleaning regime, spending twelve hundred dollars annually on sprinkling local streets “five times daily[,] seven months out of the year,” cleaning and mowing vacant lots, trimming and watering trees, and removing snow from sidewalks and crossings.6
The landscape of Jackson Park Highlands was the product of an ideology of improvement that resonated throughout the United States during