In the last decades of the nineteenth century, Massachusetts had over 220 almshouses, poorhouses, and poor farms, more than any other state; Milton has a rare surviving poor farm. Governor William Stoughton (1631–1701) bequeathed his hometown this forty-acre woodlot, and in 1805 Milton built its first almshouse here, adding barns, cattle and tool sheds, and a “tramp house” (1870s) for transients (all razed). Clustered on a hilltop in the northwestern corner, the surviving clap-boarded wooden structures—the main almshouse (1854, 1882), men's almshouse (1871, 1893), and stable (1882, 1897)—were built and expanded by Milton architect-builders John H. Burt and John A. Tucker. The pest house (1888, Frederick Severance), for the isolation of smallpox patients, sits apart.
Enclosures of one to four acres—fields, orchard, and stable pasture—ring the farmstead, each bounded by wide stone walls. The rest of the farm is swampy woodlot bisected by a cart path, with two stone platforms for loading firewood. An entry boundary stone from a 1907 survey is inscribed TOWN FARM. After the last pauper left in 1940, Milton rented the buildings and fields. Despite the insertion of