Alan Shepherd is said to have arrived in Henry County in October 1819, but land purchases in 1822 and 1823 indicate he was 'of Delaware County, Indiana'. He arrived in the area with his second wife Ann (Powell) Ward Shepherd, eighty year old father-in-law Nathan Powell and his wife, sons Alan Shepherd Jr (his oldest son with his first wife, born in 1812) and infant Samuel Shepherd, step daughters Eliza Ward (later wife of John Dorrah and William Meek) and Martha Ward (later Mrs Andrew J Lytle), brother-in-law Samuel Powell and his wife and a child. Family tradition states he left two younger sons with his first wife (Elizabeth (Powell) Shepherd), John (born in December 1814) and William D (born 1816). He served as a county commissioner from 1822 to 1823. Shepherd's farm (later known as the Hudelson farm) was the site of several mounds although it isn't clear if they are early military positions or Native American burial sites. Indians had a settlement nearby.