Chestertown is a nice old town. My wife and I enjoy going there. There are a lot of sites to check out on the net to give you information about the town. Here is one:
http://www.baydreaming.com/chestertown.htm
While we enjoy Chestertown and its history, you may want to also take a day and go to Annapolis, St. Michaels and other spots on the bay. In a 17'er you may wish to take those trips by car and/or trailer your boat to local ramps to see by water. However, a run down to the Kent Island Narrows and Rock Hall if the weather is nice may make for a fun trip. Otherwise the Chester River is a beatiful river and you will have more than enough fun just in the river.
The root of the web address above has information about many other good places to visit on the bay. (
http://www.baydreaming.com/ ) Good luck and enjoy your trip!