After reaching Dwight Presbyterian Mission, Worcester continued to preach to the Cherokee who had already moved to Indian Territory (they were later known within the nation as the Old Settlers, in contrast to the new migrants from the Southeast). In 1836, they moved to Union Mission on Grand River, then finally to Park Hill. Worcester's work included setting up the first printing press in that part of the country, translating the Bible and several hymns into Cherokee, and running the mission. In 1839, his wife Ann died; she had been serving as an assistant missionary. He remained in Park Hill, where he married again in 1842, to Erminia Nash.