The Upper Mill Street Historic District was listed on the National Register of Historic Places in 1982. Portions of the content on this web page were adapted from a copy of the original nomination document. 
The Upper-Mill Street Historic District includes many brick structures as well as frame ones, and the twin and row houses also indicate its one-block proximity to Poughkeepsie City's historic commercial district. Several of the earliest buildings exhibit Greek Revival characteristics, while those of later periods include Second Empire, Queen Anne, Eastlake, and Colonial Revival elements. The two brick churches are also distinctive; one is a Gothic Revival structure and the other a Romanesque Revival one. The latter is the only known architect-designed building; it was planned in 1859 by James H. Dudley of Poughkeepsie. The details of all periods illustrate a familiarity with high-style designs and learned craftsmanship in various materials. The street has changed from a chiefly residential one to an area of professional offices, with a few modern buildings inserted. Starting from Mill Street, on the northwestern side of the district, the boundary follows the northeastern property line of No. 265, and then runs in a southeasterly direction, one lot deep in from Mill Street, to the rear of No. 42 Catharine Street, crossing Garden Street and Conklin Street in its course. The boundary then runs northeast and southeast to include Nos. 42, 46, and 45 Catharine Street, crossing the street in its course. Then it runs southwest and northwest to incorporate the Lutheran Church and its former Rectory. After recrossing Catharine Street, the boundary crosses Mill Street to meet and follow the southeastern lot line of No. 322; then it runs in a northwesterly direction, one lot deep, to Garden Street, along Garden to Mill, crosses Mill and then follows the northeastern curb of the street to the place of beginning. Approximate acreage is six.
While the National Register-listed lower Mill Street represents some of Poughkeepsie's best vernacular, mill workers' dwellings, Upper-Mill Street Historic District is one of the city's finest neighborhoods of fashionable nineteenth-century factory owners' residences. Building substantial houses in the Greek Revival period, many updated these (Nos. 297 and 306 Mill Street) or constructed elaborate new structures in the Second Empire, Queen Anne, and Eastlake styles. Speculator John Gager was responsible for building several of the later dwellings, which he held as lottery prizes. Rivaling Academy Street and Garfield Place, Upper-Mill Street was the fashionable avenue on the north side of Main Street during the late-nineteenth century. Many of these distinctive structures remain as cultural indexes of that era's residential architecture, but have been adapted for office and other commercial uses due to its proximity to the East-West arterial and the Main Mall. Although there are two intrusive buildings in the Upper-Mill Street Historic District, one is set at the rear of a property with a period structure fronting the street.
Platt, History of Poughkeepsie, 1905.
City Directories; 1843 to 1900.
Maps: 1834, c.1850, 1857, 1867, 1874, 1876, c.1880, 1887, 1895.
Adriance Memorial Library, Local History Room, Photograph Folders.
John Gager, Lottery Prizes, 1871.