St Michaels MD
 

We plan to visit the area in mid October. We will be coming from Annapolis in the morning and thought we could stop and see Grist Mill and Easton that day. The next day I thought we would wander the town of St. Michaels, visit the Chesapeake Bay Maritime Museum and the go to Tilghman Island for the sunset cruise on the Rebecca Rourk. We would have liked to have sailed the Selina 11 as well but it is not sailing while we are there. Is there anything else that we should not miss and are these 2 days doable?

The two days are doable. The museum is 1-2 hours, the town strolls are 1-2 hours each unless you are big shoppers.

I still recommend Oxford, though the hard thing for you as westerners is that short distances on the Eastern Shore can take a long time because of low speed limits and the convoluted shore line.

It is a lovely area, and I hope you enjoy it.

Thank you much for your input.

I love the Eastern Shore and oysters will be in season and if you are early enough in October you might catch the tail end of soft shell crab season.

Mid-October the weather should still be very nice, and I would recommend eating crabs at the Crab Claw on the harbor. If it's warm, their outside deck can't be beat. It's also very pleasant to stroll around the harbor to visit some of the marina bars & restaurants.