A graduate of Bowdoin College and Bangor Seminary, Dole was a classical scholar who arrived with his wife, Emily, in the Ninth Company of missionaries in May 1841. Upon arrival, Dole agreed to become principal at Punahou and in July, moved to the Binghams’ cottage.
Dole was assigned to preach at the Seaman’s Chapel for sailors and English-speaking residents while superintending the building at Punahou. Funding was the main challenge and missionaries contributed from their small assets. By December, several mission children were assisting with preparations and attending classes before the official opening in July 1842.