Kenduskeag (town|township) was then part of Hancock County (now in Penobscot County).

Caleb could've been employed on a log drive (makes sense)--or otherwise employed somehow in the logging industry is my guess (which would explain his mobility).

Hillsborough County, NH is where I'm finding his family (New Boston), which was later Londonderry (yes--paternal family earlier, in England).

Census enumerators weren't of the highest intellect back then, so root derivatives of words (i.e., misspelling of "Derry" in the rightmost column would be commonplace).

Were his parents named Simon and Abigail?

http://www.nh.searchroots.com/HillsboroughCo/townlist.html#N...