I grew up in Westport in the 60’s.
At that time, it was primarily executives commuting to NYC on the train. My Dad and I met Rod Serling on the train one time.
Lots of wealthy folks (we weren’t).
But Staples High School hosted Cream, the Doors, Sly and the Family Stone, and other big bands at the time. I saw them all live back in the day. Pretty amazing. Locally saw the Youngbloods and Strawberry Alarm Clock (who performed a medley of their hit. ;)