You can have a terrific time on the Chester. All these locations are pretty close together so I do not know if you are looking to spend part of the day going back and forth on the river but you can be assured that it will not take you long to get from one spot to another.
Queenstown is a nice spot to visit. Honor the small red nun as you turn from the Chester to head to QT. Stay close to the green marks as you go in and swing wide around the sand spit to your port side as you enter the harbor. If you then swing around the spit, you can start to head up to the port side of the harbor. Those who hug the starboard edge of the harbor traveling past the docks to starboard will usually promptly run aground. You can land a dinghy on the landing road between the old mansion and the new new mega waterfront home but do keep your dinghy on the landing road side of the fences. You can also land around the corner at the waterman's piers. We never do that so I have little information there. At Queenstown you can walk to the outlet mall. Oh I know, kind of a funny thing to do by boat but you can pick up a book or some clothing or some interesting treats at the Pepperidge Farm Outlet or the deli, kitchen store out at the western end of the mall.
Reed Creek is a fun adventure but if you really want a challenge, try Grove Creek. Oh boy!! You pass so close to the shore, you could reach out and touch the bank with your boat hook.
Chestertown is a nice stop. Don't know if the Sultana is in but that is fun to see. Also the Farmer's Market in the town square if fun to get fresh vegetables and baked goods.
Grey's Inn Creek is quiet, usually. The Corsica seems to have more and more power boats backing up to a little sandy beach and it is party central.
I am jealous. We have enjoyed the Chester for years but have been having a refit done on our vessel so my data is about 1.5 years old. I did talk with a friend who had reported shoaling (this year) at Kent Narrows but now he thinks it was due to the wind blowing hard, reducing depth in the North Channel.
Have a great time!! Be sure to share your tales of adventure.
s/v Tango, CR 34
still lying in Oxford, MD