A historical-cultural book, Albion's Seed, indicates that the flow of Puritan emigrants to the West followed the Great Lakes and ended in Iowa. (Obviously there was then a "jump" across the Rockies to the Oregon Territory.) Maybe that's why Iowa votes like New England.
Btw, excellent book, though a little dry, especially if you're not into cultural-history: http://www.amazon.com/Albions-Seed-British-Folkways-Cultural/dp/0195069056
Iowa doesn't really vote much like New England, at least not anymore. It's a swing state, after all.