Trail presence Eastern Shore 1700's.
With all that has been uncovered an interesting picture has emerged of the Eastern Shore Traills. The picture develops around Chestertown and the year 1730. By this year Chestertown was one of six proclaimed Royal Ports in America. The Chester River is extremely deep off the Chesapeake and the greatest vessels could penetrate inland to Chestertown. Not far from here lay the farms of Joseph Tryall who must have commuted to Chestertown often with goods. Even James Trail of Dover, Delaware found it prudent to own a house in Chestertown. The Chesapeake trade was giant and the earliest settlers closer to the coast,like James Trail,by 1730 were a bit distanced. Th point is that James Trail of Delaware and Joseph Trail of Queen Annes County would have been frequenting Chestertown by 1730 as grown men. By the common family associations the two men had it seems they likely met at Chestertown. Chestertown was a shipbuilding town and gained fame as such. Enter the picture now is Robert Trail of Philadelphia who by 1730 owned and operated a sloop out of Philadelphia and surely must have frequented Chestertown and the Chesapeake as well. In George Washington's memoirs he describes a journey from Virginia up to Philadelphia in which he went by way of Chestertown which was apparently the common route at that time. Robert Trail of Philadelphia is a mystery but cannot be dismissed as coming from the Eastern Shore Trails. The name Claypoole comes to play here. Robert Trail of Delaware was closest friend to Norton Claypoole. Norton's brother James Claypoole lived at Philadelphia and owned many sloops.Could this have been how Robert Trail of Philadelphia came to his sloop? James Trail of Delaware sold his house at Chestertown to James Claypoole,nephew to Norton and James Claypoole. It would be something if all these Trails conversed at a pub in Chestertown at some point.