Watch Hill sits at the most southwestern point of Rhode Island on a peninsula overhanging into Block Island Sound. On a clear day you can see Montauk on the horizon. Watch Hill was once written about in the New York Times as a community "with a strong sense of privacy and of discreetly used wealth" in contrast with "the overpowering castles of the very rich" in nearby Newport.
Today it is best known as the backdrop for the Ocean House and The Flying Horse Carousel, the oldest operating suspended-horse carousel in the US. I visited as a kid and there's a good chance I was wearing seersucker too. If you grab a coveted outside horse you can reach out and grab silver rings and collect them on your horse's ears. There is one special brass ring that will score you a free ride.
What will your Watch Hill story be?