Holland Island was originally settled in the 1600s, taking its name from early colonist Daniel Holland, the original purchaser of the property from the Dorchester County Sheriff. By 1850, the first community of fishing and farming families developed on the island. By 1910, the island had about 360 residents, making it one of the largest inhabited islands in the Chesapeake Bay. The island community had 70 homes, stores and other buildings. It had its own post office, a two-room school with two teachers, a church, baseball team, community center, and a doctor. The islanders supported themselves mainly by dredging for oysters, fishing for shad and crabbing. Their fleet of workboats included 41 skipjacks, 10 schooners and 36 bugeyes, some of which were built on the island. The wind and tide began to seriously erode the west side of the island, where most of the houses were located, in 1914. This forced the inhabitants to move to the mainland. Many disassembled their houses and other structures and took them to the mainland, predominantly Crisfield. Attempts to protect the island by building stone walls were unsuccessful. The last family left the island in 1918 when a tropical storm damaged the island's church. A few of the former residents continued living on the island during the fishing season until 1922 when the church was moved to Fairmount, Maryland. Stephen White, a minister, cared for the island for many years and formed The Holland Island Preservation Foundation. In June 2010, White sold the island to the Concorde Foundation. In October 2010, the last remaining house on Holland Island, built in 1888, collapsed.
The land of the island has been submerged as a result of erosion exacerbated by sea level rise associated with the sinking of the land's surface associated with isostatic subsidence. This process has caused a major loss of land on the island. Like other Chesapeake Bay islands, Holland Island is primarily made up of clay and silt. The western ridge of the island is very exposed to waves in the bay, making it prone to erosion as well. The island's size was reduced by half, from approximately in 1915 to in 2005. Most of the remaining land on the island is now marsh, but most of the time the entire island is underwater. Many birds, including terns, herons, songbirds, and brown pelicans used to be found on the island. A survey in 1995 counted 609 nesting pairs in a heron rookery on the island. Hurricane Isabel, a tropical storm by the time it reached Marylandin September 2003, destroyed 60 percent of the trees that previously served the rookery.
