In 1858, Milo and Martha Manning arrived from Kentucky with eight children, including their son Wentworth, for whom the community is named. Wentworth became a businessman and landowner. Starr School, the first free school in the area, opened there in 1886, and the schoolhouse also served as an early house of worship. Worthy Green Kennedy's general store opened in 1903 and housed the Monico post office for two years. Todd Hill School opened in 1907 and later merged with Starr to form Wentworth School in 1917. The community also had churches, a grist mill, cotton gin, blacksmith, and sawmill. The school consolidated with Canton in 1949, and the Kennedy store, which also served as a community center, closed in 1952. Wentworth remains a testament to generations of families.