One of the weird things about the Chesapeake Bay is that a lot of boaters stop using it after Labor day, so I have the whole place to myself. Sailing out of the Patapsco River and rounding Bodkin Point, my only company is three skipjacks dredging oysters on Mountain Bar off Gibson Island. This cruise was a few years ago. I don't imagine we'll ever see skipjacks dredging oysters again in the Chesapeake.
It's perfect cruising weather, and is the same weather I have now in New Mexico - temperatures in the 40's at night, and in the low 60's in the afternoon.
This time of year we get a breeze out of the northeast sometimes, so it's a comfortable reach down the western shore until late afternoon when I motor into the little creek on the north side of the Magothy where the ugly orange glass house is (the same one that overlooks Ropes beach in Cotuit.) Dan Smeraglioulio will know which creek I'm in. It's a perfect snug little anchorage.
I need the Origo alcohol stove on once the sun goes down for warmth. Dinner is store bought fish cakes and baked beans, easy to cook and eat. The NE breeze lets go, and we lie at anchor in an utterly still cove. Later in the night, a light snow falls.