Holland Island is located in the Chesapeake Bay in Holland Strait, between Bloodsworth Island and Smith Island, six miles west of Wenona, Maryland. The island was once about five miles long and one and a half miles wide, and inhabited by watermen and farmers in a thriving fishing community. But over the decades, rising Bay waters and natural sinking of the land ate away at the island until it was nothing but a blotch of land in the sea. The last house on Holland Island stood defiantly for over century until its collapse in October 2010.

Holland Island was originally settled in the 1600s, taking its name from the first owner of the property Daniel Holland. 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. At its peak, the island had 70 homes, several stores, a post office, two-room school with two teachers, a church, and a community center. It had its own baseball team 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 last house on Holland Island in October 2009.