One of the interesting places to see along the trail is the Shirley Plantation which is the oldest continuously working plantation in the US.
They family runs a vineyard on the property with a tasting room and restaurant that serves breakfast and lunch.
I wonder if Maryland could ever do a St. Mary's to Annapolis bike trail? Right of ways are the biggest problem with doing a trail. Following a state road makes this more doable as the State usually controls the land on either side of the road.