Within New England, the Industrial Revolution incentivized affluent individuals to invest in the development of mill towns, including constructing worker housing to support their entrepreneurial endeavors. However, standard housing development practices proved inadequate in addressing rapid growth, revealing worker exploitation as a harmful driver for urban development (Mitchell, 2013). Investment in the region’s mill towns has slowly depleted, leaving remnants of the Industrial Revolution as a visual reminder of the past. In a time of housing inaccessibility, professionals in architecture and planning have adopted a sense of responsibility in addressing today's lack of infrastructure. The adaptive reuse of mill buildings has become common in increasing housing inventory in New England. The scale of the redevelopment requires an immense investment in historically neglected areas, emphasizing the need to preserve welfare for vulnerable populations. This thesis explores the suitability of New England's historical mill districts for the adaptive use of affordable housing, analyzing the strategies currently implemented using comparative case study analysis to address their effectiveness in aiding the needs of financially burdened residents. Further, this thesis aims to demonstrate techniques for memorializing a site's complex history and reflecting upon the balance between the revolving needs and values of post-industrial cities.