Call Hartge Yacht Harbor in Galesville, Md. About 15 miles south of Annapolis. They might have something.

 

Are you looking for a mooring rather than a slip? The Chesapeake is more of a "slip" type area vs Maine for example. For proximity to NY I'd go with northern eastern shore. Rockhall and north.

 

There are some moorings in Swan Creek just North of Rock Hall, I think they're owned by Swan Creek Marina? Someone here surly will know. How much draft do you have? I wouldn't go into Swan Creek with much over 6' draft. I have 4 and have bumped on occasion passing the Red 4

 

why not set your own, there are helix mooring contract guys on the bay. the rules are easy, stay out of channels, oyster beds and cable areas and thats about it and its free.

i said contract it as with you being so far away checking on it would be harder

 

The hard part, it would seem to me, is where to keep your dingy. You can put down a mooring almost anywhere, but you will need a place to launch and or keep your dingy.

I have a slip near galesville, MD (West River, just south of Annapolis). There is a public dock there and and place to park. I have seen several private moorings put down over the last several years...

 

Green Point Landing Marina on Worton Creek. Good protection & reasonable.
Green Point Landing Marina

 

Call Georgetown Yacht Basin. They're on the Sassafras River in Georgetown MD on the Eastern Shore. They maintain a number of moorings and the river is mostly fresh water. Georgetown folks are very friendly and accomodating. It should meet your requirment for convenience to NYC.
Their number is 410-648 5112
Their website is Welcome to Georgetown Yacht Basin, Inc.