There were tensions on the border between New England and Acadia, which New France defined as reaching the Kennebec River in southern Maine.

[4] English settlers from Massachusetts (whose charter included the Maine area) had expanded their settlements into Acadia.

[5][6] For their part, in response to King Philip's War, the five Indian tribes in the region of Acadia created the Wabanaki Confederacy to form a political and military alliance with New France to stop the New England expansion.

[7] On Abbé Petit's advice, Father Louis-Pierre Thury settled at Pentagouet (Castine, Maine) in 1690, near Jean-Vincent d'Abbadie de Saint-Castin, where he remained eight years.

In 1689 he accompanied Saint-Castin on the raid that resulted in the destruction of Pemaquid (1689); he left a detailed account of events.

Benjamin Church's third expedition to Acadia during the war was in 1692 when he conducted a retaliatory raid with 450 men against the Penobscot village.

He took part in the attack against Pescadouet (Oyster Bay) in New Hampshire, and was present with Robinau de Villebon and a party of Abenaki at the capture of Pemaquid by Pierre Le Moyne d'Iberville in 1696.

[9] Madockawando and others from Penobscot fought alongside Hertel Portneuf and St. Castin at the Battle of Fort Loyal (May 1690).

[13] Starting in 1775, Condeskeag became the site of treaty negotiations by which the Penobscot people were made to give up almost all their ancestral lands, a process complete by about 1820, when Maine became a state.

The tribe was eventually left with only their main village on an island upriver from Bangor, called "Indian Old Town" by the settlers.

Eventually a white settlement taking the name Old Town was planted on the river bank opposite the Penobscot village, which began to be called "Indian Island."

The climax of the 1825 novel Brother Jonathan by Maine native John Neal is set on Indian Island during the American Revolutionary War.

The novel features a protagonist of mixed Penobscot-English descent and describes the island as "the last encampment of the Penobscot Red men".