In late 1915, Howe traveled back to Massachusetts to court Alice Worcester, daughter of the head of the company he had worked for in the summer at MIT. After some surprise at the attention from a man she barely knew, Worcester eventually accepted him, and the two were married in mid-1916. The same year, he resigned from government service to go into business with partners as C. D. Howe and Company, whose major business was initially the construction of grain elevators.[13] Both the company headquarters and the marital home were in Port Arthur.[14] Howe's first contract was to build a grain elevator in Port Arthur.