I don't think the area is highly political. However there are a lot of retired politicians in the area, most notable current ones probably being Cheney and Rumsfeld in St. Michaels. But generally speaking I think Republicans usually win for national and state elections but here in Easton I think the county council is split and the Easton council is mainly (if not all) Democrats.
There are a handful of grocery stores on Kent Island with Safeway being the newest and biggest, Centreville has a Food Lion and Acme. Easton has 4 or 5 plus WalMart and Target. Depending on how far north in QAC you go you start getting closer to Chestertown which I know used to have a SuperFresh. Unless you are looking for something like Whole Foods or Trader Joe's, you can find what you want without crossing the bridge.
Chestertown and Easton also would be the closest hospitals if that is of a concern.
Here are a bunch of local videos I came across if you are interested.
MidShore Network Message Board - Tourist Video