Sherman, CT

Sherman, Connecticut is the northernmost and least populated town in Fairfield County. It has been named "The Best Small Town In Connecticut" many times. Celebrities such as Derek Jeter of the NY Yankees and the CEO of Disney have weekend houses there. There's only one public school, and students have to go elsewhere for high school. The town is on Candlewood Lake, which is a large man-made lake, and the Appalachian Mountains also run through the town.