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Caleb Church moved from Hingham about 1668 to Dedham and there engaged in business as a miller and millwright. Among the earliest records of Oxford, Massachusetts, is a contract with Caleb to build a mill there. The town of Dedham had reserved 20 acres of land for a millsite and sold a part to Caleb in 1677.
About this time he went to Watertown, Massachusetts, where besides milling, he was licensed to keep an inn, which he did until 1711. He sold the inn in 1712 to Thomas Learned, who kept a tavern there for 50 years. On March 22, 1705-6, Caleb mortgaged 12 acres of pasture land known as the "Dirty Green".
He was received into full communion 4 March 1687, but did not become freeman until 22 March 1690, apparently in preparation for his election as Selectman. He held that office for 7 years and was Representative for Watertown in 1713. His purchase of the water power at Fall River has been mentioned, but he soon sold his half to his brother Benjamin Church for L100. (History of Bridgewater, Hingham and Watertown Records of Hingham, Dedham and Watertown)