If you only know Ossining as New York's funniest-sounding place, or even if you only know it as the home of Don Draper from "Mad Men," you're missing out on one of the best just-beyond-NYC small towns.
Set right on the Hudson, this quiet village was originally called Sing Sing, but changed its name in 1901 after a boycott of goods made at nearby Sing Sing Prison started to hurt town businesses as well. Today, Sing Sing Prison is still around, and Ossining is a sleepy little village with a quaint Main Street strip surrounded by an impressive array of wilderness.
Everything in Ossining is close enough to find in a quick walk or drive, but what follows are a few of our favorites.]]>