In the 4th or 5th century, Inishfree Upper was reputedly controlled by Niall of the Nine Hostages, future High King of Ireland.

[2] Later, the late medieval period, saw Inishfree as a possession of the descendants of Niall of the Nines Hostages, namely the clan of Red Hugh O'Donnell, the leader of the last stand of the Ulster chieftains against the English.

[4] In September 1978, the Argentine musician Guillermo Cazenave was living on the island, where he recorded his album Inishfree.

[6][7] The last permanent resident of Inishfree Upper was Barry Pilcher who had moved there in 1993 from Essex and to where he returned in 2013.

[8] In 2016, two people voted in the Irish general election on Inishfree, both of whom had moved to live primarily in Burtonport.