 He started his career in the ministry as a Congregational preacher in New Hampshire but converted and became an Anglican clergyman in 1760, through his connection with Dr. Silvester Gardiner, a prominent Massachusetts physician, businessman, and landowner.Gardiner, also Anglican, sought a minister to serve the rural parish of Frankfort or Pownalborough (now Dresden, Maine, but then part of Massachusetts), which was part of the lands his business partnership, the Kennebec Proprietors, oversaw.Bailey's congregation was a mix of mainly German Lutheran and French Huguenot immigrants, who were often at odds on matters of religion with the area's Yankee Congregationalists.