Potawatomis had a sizable settlement where Waukesha is now, but an 1833 treaty forced them to cede all their land in southeastern Wisconsin. European American homesteaders began staking claims here the following year. Natural resources, especially water power from the Fox River, attracted investment, and by the mid-1840s Waukesha boasted thriving flour and woolen mills, a limestone quarry, and other industries. The Milwaukee-to-Dubuque Military Road begun in 1838 and a railroad linking Milwaukee to the Mississippi River in the 1850s connected Waukesha’s markets to the wider world. Then Waukesha became the seat of its new namesake county in 1846, and in the 1860s promotion of its mineral springs turned the city into a resort for health seekers.
A commercial district grew up at Five Points, the crossroads east of the river. At first most buildings were wooden, but in 1857 the three-story limestone Robinson Block (now the Almont) was erected at 342–344 W. Main. The round-cornered building has metal cornices; the clerestory above the storefront display windows and the glazed-tile panels below were early-twentieth-century modifications. Following completion of the Robinson Block, downtown Waukesha acquired a strong sense of visual cohesion. For the next fifty years, most of the buildings were of Niagara dolomite, the locally quarried limestone, and most were Italianate.
The Nickell Building (1901) at 338–340 W. Main takes advantage of its corner location by crowning an elaborate turret with a bracketed dome. The Jackson Building at 321 W. Main was built in 1858–1859 for a druggist and grocer. Its tall, narrow windows, hood moldings, and bracketed cornice typify Italianate commercial buildings.
At Five Points (the intersection of W. Main, Broadway, and Grand Avenue) is the downtown’s most dramatic building. The High Victorian Gothic Putney Block (1882), at 301 W. Main by Stephen V. Shipman, has shoulder-gabled parapets studded with crockets and finials, a bracketed cornice, and a metal mansard roof. The parapets bear insignias of the Masons and Odd Fellows, who met upstairs. In 1891, Frank Putney built the New Putney Block at 802 N. Grand, another corner building. Its quarry-faced limestone walls, elaborate parapets, corner bartizan, and clustered chimney pots embody a Queen Anne commercial aesthetic.