15 August Chestertown, MD

There's a lot of Chesapeake Bay to explore; 11,640 miles of tidal shoreline surrounding 4,480 square miles making it the third largest estuary in the world.

We left Annapolis and motored up the Bay to the Chester river on the eastern shore. This is a long, meandering river and it's more than twenty miles from the entrance to the seventeenth century Chestertown with farmlands on either side and only a few houses on the banks. Lots of bird life to watch – my favourites, the ospreys are plentiful, plus waterfowl.

There's a small marina, a town dinghy dock and plenty of room to anchor. In the five days we've been here we seen one other sail boat anchor and several motor boats dash in, stay overnight and leave early next day. We are working on a slower timetable.

The original settlement dates from early 17^th century but is was during the Revolutionary and Civil wars that it became an important travel hub. George Washington passed through many times. There was a road from New York to Chestertown and a road from the capital at Annapolis to the south. In between Chestertown and Annapolis there was a ferry, a quicker option to riding around the mighty Chesapeake and Delaware rivers. There are many houses in Chestertown from this period.

It's a locals town today, fairly quiet and with any artists living here. There are a number of art galleries and from what I saw a lot of talent too. David and I wandered, stopped for a coffee here and there, found a bakery with incredibly good baguettes (I exported an armful in the newly restored freezer when we left).

There was a railway at one time running down to the waterfront. The tracks have been lifted and the track is now a walking and cycle trail which conveniently links the dinghy dock to a big supermarket about two miles north of town.

We liked Chestertown. It is a long way up the river, but the town is quaint and the people very welcoming. We spent a lot of time chatting. On Sunday it rained all day. On Monday we picked up anchor bound for St Michael on the Wye River.