Looking this morning at possible anchorages on our first night out. We'll leave out of Chesapeake about 5 or 5:30 a.m. (I can hear Bruce groaning from here, and he's still on the west coast), make the drive to Rock Hall, rig, load the gear/supplies and drop the jeep/trailer at Mary Lou and Fred's house not too far away. With all that I expect we'll be on the water around noon or so.
Sailing north there are four possible anchorages anywhere from 15 to 18 miles from Rock Hall, which would be the right distance for an afternoon sail. Three of the possibilities are creeks on the eastern shore - Fairlee, Worton and Still Pond - and all look to be nice places to visit. Excellent protection and undeveloped shores lines, all are surrounded by a few homes and farmland.
There is also Pooles Island which I think belongs to the U.S. Army and is associated with the nearby proving grounds. I am not sure if it is accessible at all. I've emailed Kevin of Slip Jig fame, who sails up in that area, so see if he has any advice on the island. There is an old lighthouse on the island, and it seems like it would be a nice place to visit.
As for the first night's meal, Bruce may be thinking of the shrimp and chicken gumbo which he had made on an earlier trip. But I'm also hearing that the striper fishing is excellent up on that part of the bay right now, so we ought to keep our options open for fresh fish on the griddle.
ps - I just checked my reference, Washington Tuttle's recollection, and he spent his first night in Worton's Creek, then made Chesapeake City by the following afternoon. Also noticed a nice quote from Tut about boiling water on a small boat, one that rings very true to me.....
"It has been said that the amount of water boiled aboard a small boat would make you think that Marcus Wellby, M.D. was in the forepeak delivering twins."