Rockhall, Worton as well as a few in or near the Kent Narrows all on the Eastern Shore, not much on the Western Shore other than Middle River. Cant recommend one specifically for kids or family fun.
Chestertown IMO is to far up the river for a sailboat, same with Georgetown on the Sassafras.
Tartan 37 - S/V Windgeist
Sailing the Chesapeake Bay
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Photo by Joe McCary