Essex, Massachusetts, is a lovely New England town which had an excellent second-hand bookshop when I passed through some ten years ago. It stands on the Essex River, which leads out into some lovely coastal waters. The annual Essex River Race for boats from kayaks to gigs starts and finishes in the town, passing round Cross Island in Essex Bay. It is only about 6 miles but gets close to the Atlantic so conditions can be fairly brisk.
David Jones, a member of the Irow forum, has posted a bunch of pics here. Race details with a map are here.