The town of Westport in Fairfield county was the very first town I visited in Connecticut. I came to Westport in 2010 so it holds meaningful memories for me. Westport is only 50 miles from NYC so it was the perfect suburban neighborhood without the city bustle. It is known to be on the top richest towns in CT list. That makes a drive around Westport very stunning with all of the mansions and structures. The downtown main street is another beautiful spot to see.