Chestertown is quaint, with little stores and restaurants, brick sidewalks, and a park in the middle that acts as a community center. They were having an art festival there earlier- and that night we enjoyed a great bluegrass band there from Annapolis.
We wandered down to the water (here it's actually a river, which flows out into the Bay). It was lovely! We wandered around the boardwalk and fed the ducks.
The geese were kind of scary. I caught one of them in mid-flap. :)
I'm not gonna lie- there isn't a ton to do in Chestertown so the ducks were a big draw.
We went to dinner at The Fish Whistle. We had called ahead of time, which was great because it secured our table out on the water. We ordered the fried calamari ($8) for an appetizer- quite tasty! I liked the spicy chili sauce they were served with. Just the kind of dish you want to be eating as your looking out over the sunset on the water and the boats.
For the main course, I got Drunken Mussels ($7.50), something I've found out I really love since moving to Baltimore. These mussels were in a garlic broth, served with crusty bread. Technically this was an appetizer- I wish they would make it a main course and up the size a little bit, but otherwise I quite enjoyed it. Kevin got the pulled pork BBQ sandwich ($9), and while he liked it, it was nothing memorable.
The prices were reasonable and the service was decent, so I would recommend it, especially if you can get a seat outside when the weather is nice!
We had a nice time in Chestertown and I would recommend it for people in the Baltimore/Annapolis/DC area who are looking for a night away from the city.