The district includes six contributing buildings and two monuments, based around the intersection of South and Church Streets[clarification needed] in Aquinnah.

English settlement began in the 1640s in the eastern part of the island, and the Gay Head area in the far west remained reserved to the natives.

Following American independence in 1783, the Wampanoags became de facto wards of the state, but their lands at Gay Head remained under their control.

The church congregations declined in size, and were eventually absorbed into that of nearby Holmes Hole (present-day Vineyard Haven).

Non-contributing elements include the modern town office building and the Gay Head Fire Station.