If I had just one night to spend north of the bridge, I would go for Rock Hall in the afternoon and Swan Creek to
anchor for the night.
There is a restaurant called the Waterman's directly inside the main channel in Rock Hall harbor. They have dockage for diners.
Just north of Rock Hall is Swan Creek, a pleasant and scenic anchorage.
You don't have to sail or motor a long way up a river to get to Rock Hall. It's right on the bay, although there is a long bar protecting the harbor. You may have to go a ways south out of your way to round it if you draw too much water. Locals cross it often.