Chestertown Maryland is a small town located on the Chester River in Maryland. This town boasts some of the most historical properties in all of Maryland. Rich with history, layed back attitude and some of the best crabs you will find on the eastern shore. Chestertown is an inviting and proud community that likes their town just the way it is. If your looking for shopping malls, big box stores and a Walmart better keep going because you won't find anywhere within 25 miles of Chestertown. The largest structure you will find is the football stadium of Washington College..