The settlement at the confluence of the Choptank and Tred Avon Rivers was recognized by the Maryland colonial Assembly and laid out as the town of Oxford in 1683 -- one of the oldest towns in Maryland. In 1694, only Oxford and Annapolis were approved by the Assembly as Maryland ports authorized for import and export.

Oxford’s Eastern Shore import-export monopoly, especially for tobacco from surrounding plantations, made it an important trade and financial center before the American Revolution.  At this time, Robert Morris, Sr., whose son was the “financier of the Revolution”, was a prominent Oxford agent for a Liverpool shipping firm. Other residents included sea captain (later federal customs agent) Jeremiah Banning and Col. Tench Tilghman, aide-de-camp to Gen. George Washington.

The Revolution ended Oxford’s colonial trade monopoly.  The shift from tobacco to wheat as the Eastern Shore’s main cash crop further weakend the town’s influence as a financial and trade center.  Ships from England and the West Indies no longer landed at Oxford.  The town sank into a century of obscurity and might have disappeared entirely from the map.  If not for the oyster.

Oyster harvesting and regional shipping around Chesapeake Bay replaced international trade as the town’s economic base.  A railroad line and several seafood packing companies arrived in the decade following the Civil War.  Several shipyards grew in Oxford to service the seafood industry.

At the northeastern end of the Strand, then called Front Street, William Benson and Henry Bateman established a shipyard in 1866. Benson & Bateman Shipyard was located along Water Street, near Town Creek, in 1877 and continued operating until at lease 1892.  Benson and Bateman built bugeyes, which are round-bottomed, two-masted oyster-dredging sailing craft, and other vessels of Chesapeake Bay design.

This second economic boom played out by the 1920s when oyster beds nearby on the Tred Avon and lower Choptank were exhausted.   But the Oxford shipbuilding tradition did not die.   It continues in the form of world-famous yacht construction and marine services companies such as Cutts & Case, Inc., and Crockett Bros. Boatyard.

This river trip leads you to explore the Oxford waterfront and nearby Tred Avon River, by water and by land.