In the fall of 1626, Governor Conant moved himself, his wife and four young children (4 year old Caleb, 3 year old Sarah, 1 year old Lot and the young baby Johanna), along with 40 other ambitious pioneers (including his old friend Reverend Lyford, Humphrey Woodbury, John Woodbury, his future son-in-law John Balch, Peter Palfry, Walter Knight, William Allen, Thomas Gray, John Tylly, Thomas Gardner, Richard Norman and Son, William Traske, and William Jeffry) from Cape Ann to Naumkeag – the ‘fishing place’ (later to be renamed Salem). They cleared the forest, tilled the ground for farming and set about planting maize and tobacco.
At Naumkeag, the colonists built houses, cleared and prepared the land for the planting of corn and tobacco and other crops. It is believed that Conant built the first house in Salem, on what is now Essex Street almost opposite the Town Market, that year and his son Roger was also born that year, making him the first colonist born in Salem.
Conant was constantly involved in town government, he became a Freeman on May 18 of 1631, served on the General Court of Massachusetts in 1634, and served as a selectman, a justice on the Court of Quarter Sessions and a delegate to ordinations.