As limestone became the city's leading industry in the 1920s, an apple orchard was removed to permit the extension of First Street eastward up a long hill and the platting of a new neighborhood.

At the top of Vinegar Hill were the mansions of the wealthy limestone executives; like the workers' houses below them, these homes featured ornate stonework with images such as those of the children of the homeowners.

[2]: 89  They used these materials to construct residences in a wide range of architectural styles, including American Craftsman, Neoclassical, and Art Deco.

Among the books that have concentrated on the architecture of Vinegar Hill is Carol Shields' novel The Stone Diaries, in which the neighborhood is part of the setting for much of the novel.

"[4] The district includes a disproportionately large number of above-average properties: about 13% of the city's sites were named either "Notable" or "Outstanding," in contrast to 40% of those on Vinegar Hill.

[4][7] In 2003, a movement started to have Vinegar Hill accorded the national recognition that it was seen as lacking, and the city received a historic preservation grant from the state government for use in the district.