After you have passed the Narrows heading up the Chester you will find Queenstown on you right about 3 miles or so past the Narrows. Queenstown harbor is to the right as you clear the channel, you want to go to the left and go in a bit. Queenstown is quiet, looks a bit like a small New England town. Holding here and in most places in the Cheater is good to very good.
About another 3 miles or so up the river is Gray's Inn Creek on your left. This too is very quiet mostly due to the sewage treatment plant further up the creek, but unless you are planning on a swim, that is not a reason to go in.
Another mile or so up the river is Reed Creek on the right. Pay attention to the marks going in and then head off to the right after you get in and head up the creek. Classic Easter Shore anchorage. Nothing there.
Back in the river and another mile or two you come to the entrance to Landford creek on your left and the Corsica on your right. You've been to the Corsica, so you know what that is like. Cacaway island in Landford is a favorite, as is Lovely Cove further up the creek, you could spend half a summer in Langford Creek alone, with all the anchorages available. There are two branches to Langford Creek start with the one on the right going in. You will probably see bald eagles here, it's like that.
After passing Langford and the Corsica, the creeks sort of get shallow, but the river is still 40 foot deep. You can anchor along the river depending on how the wind is blowing, but for most people the next stop is Chestertown. Chestertown is simply beautiful, with the second largest number of colonial buildings in Maryland, the first being Annapolis. Lots to do in Chestertown, you can anchor in the river or there are a couple of marinas. Many good restaurants and shops. It is a college town. Big Memorial Day and 4th of July doings. Depending on tide and current it would take about 5 hours to get from the Narrows to Chestertown under power.
The Chester is my back yard so if you need more detail let me know.
BTW you say you race Lightings. The Rock Hall YC, located on Langford, has a very active Lighting program and host Nationals there, along with log canoe races.
Have fun, you'll love the Chester