Trump's best region will likely be the Naugatuck Valley, which generally runs along the CT-8 corridor in New Haven and Litchfield Counties (with a few Fairfield County towns thrown in). That's towns like Seymour, Watertown and Middlebury. It is the Republican heartland of Connecticut, to the extent Connecticut has a Republican heartland. You can see the area
I'm referring to on the 2010 Connecticut PVI map in
this old post. I haven't recalculated town CT PVIs for 2012 - yet.
Trump's second best region will likely be in the more rural parts of Eastern Connecticut.