If you can come through Kent Narrows from the upper Bay, St. Michael's is a great place to stop over. If you have kids, get a membership at the Ches. Bay Maritime Museum, where you can stay over night in their slips. After the museum closes in the evening, your kids will have the run of the place -- tons of fun and loads of energy burned!! We usually get a wiffle ball game going on Navy Point in the evenings.
Farther down the Bay, I also recommend Solomons. If you want to explore up the Patuxent, St. Leonards Creek is a nice spot.
If you head further south, St. Mary's City is nice too, with historic sites to visit. The college hosts a summer concert series out on the lawn overlooking the water (free admission, I think), on Friday nights.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT