Chestertown is a pleasant burg on the Eastern Shore of Maryland, where we traveled for a day trip on Thanksgiving weekend. It was “small business Saturday” so poking around in some of the little shops in town seemed the thing to do. Unless you are an extremely pokey shopper, that can be achieved in a couple of hours, max.
If you stop at the Visitor’s Center on the way in to town, they will give you a map of town so that you can see just how small it is, as well as a walking tour brochure that guides you around the stately 18th century houses paralleling the river. (Federal, Georgian, with or without Flemish bond bricks, take your pick.) A walk down to the pier to view the schooner Sultana is also a must – tall ships are always intriguing. There are several nice looking restaurants where one might get some local seafood, but we held out until Kent Narrows on our way home and indulged in some crab cakes, oysters, and scallops at the iconic Harris’s Crab House.
As we toured the town, I started noticing some interesting critter depictions. First, some very boldly colored and rather saucy lions in a fountain in the park downtown. Second, a giant crab claw emerging from the water near the pier (see landing image, above). Third, the eagle carving on the schooner. Fourth, a metal sculpture of honeybees outside a modest but well groomed house. If you get to Chestertown for a visit, you can use these as a sort of critter scavenger hunt on a leisurely walk around town. Enjoy!