Saylesville was named for Stephen Sayles and his four sons, Asa, Donerson, Whitman, and Mortimer, and daughter Juliana, who settled here in 1839. The first settler was Alexander Rankin in 1837. Other early settlers included Scotsman Alexander McFarlane in 1840, a woodworker and farmer; Yankee Adam Schultis in 1841, a farmer; German David Orendorf in 1841, a miller; Scotsman William Johnston in 1842, a quarryman; Englishman William Brown in 1849, a blacksmith; and Yankee Ed Gernon in 1854, a farmer and state senator. A mill was built in 1841, burned, and was rebuilt in 1887; it was first a flour mill and later a grist mill. The first school, built of grout opposite the cemetery, was built in 1847, and a second school to the east was built in 1896. A community hall was built in 1890 for Sunday School use, became a community hall in 1915, and was used for many purposes including weddings and funerals, while dances and card parties were banned. Other early buildings included a creamery built in 1847, a blacksmith's shop built in 1849, and a cobbler's shop and general store.