Hoopers Island is a chain of two islands in Dorchester County, Maryland, United States. Upper Hoopers Island and Lower Hoopers Island are surrounded by water with the Chesapeake Bay on the left side and the Honga River on the right side. The remote set of islands has much wildlife and is well known for sport fishing and crabbing industries. Hoopers Island was issued one of the earliest land grants in Dorchester County, Maryland. Geography Hoopers Island is located on the Eastern Shore of Maryland. The islands are situated on the south-west shores of the Chesapeake Bay in Dorchester County. Hoopers Island is roughly long and consists of three small islands. The islands are very narrow in many places and one can easily see water, the Chesapeake Bay and the Honga River, on both sides of Maryland Route 335 which travels through the islands. Upper Hoopers island is located at N. 38°20' W. 76°14 and Middle Hoopers island is located at N. 38°16' W. 76°11. Lower Hoopers Island is now a marshland. History The early residents of what is now known as Hoopers Island were the Yaocomico people. According to some local folklore, the land was purchased from the Yaocomico tribe for five woolen blankets. Hoopers Island is considered the oldest settled area in Dorchester County. The namesake of the islands is Henry Hooper. Hooper was friends with the Calverts, an important family many consider to be founders of the state of Maryland. In the mid-17th century, parts of the islands were surveyed for Hooper. The first parcel of land was surveyed by Robert Clift and aptly titled Hooper's Clifts. An additional of land was surveyed for Hooper later on in 1668. He received additional parcels of land in 1669 as well. Though much of the land was claimed by the Hoopers, other families such as William Chaplin, Richard Bentley and Philip Shapeley owned major plots of land. In addition, some indentured servants such as Thomas Hooten and Daniel Puddiford received land. The Hooper family The Hooper family made Dorchester County their family home in 1669. Henry Hooper had a large family: he was married twice and had 14 children. Henry Hooper was one of the first commissioners of Dorchester County. Many descendants of the original Henry Hooper followed in his footsteps and served on the Dorchester County legislature as well. Upon his death, Hooper left parcels of land, with names