[2][3][4] Before colonization, the lands that accounted for Old Dartmouth had been inhabited by the Wampanoag Native Americans, who are part of the Algonquian language family.

[7] The first European settlement in the Old Dartmouth area was at present-day Cuttyhunk Island by the explorer Bartholomew Gosnold in 1602.

Arriving at Cuttyhunk, Gosnold found evidence of indigenous inhabitants and noted an abundance of natural resources.

He decided that due to the island's ample defense capabilities and fertile land it would be a perfect place to begin a new colony.

A region of 115,000 acres (470 km2) changed hands in a treaty between the Wampanoag—represented by Chief Ousamequin (Massasoit) and his son Wamsutta—and high-ranking "Purchasers" and "Old Comers" from Plymouth Colony: John Winslow, William Bradford, Myles Standish, Thomas Southworth, Henry Howland, and John Cooke.

[15] Members of the Quaker faith, officially known as the Religious Society of Friends, were among the earliest European settlers of the Old Dartmouth Area.

[21] At first, the Old Dartmouth territory lacked major population centers and instead consisted of isolated farms and small, decentralized villages.

The increasing European population and their demand for land led the colonists' relationship with the indigenous inhabitants of New England to deteriorate rapidly.

[2] In this conflict, Wampanoag tribesmen, allied with the Narragansett and the Nipmuc, raided Old Dartmouth and other European settlements in the area.

In the same garrison several natives surrendered to Captain Samuel Eels, but were subsequently betrayed and brought to Plymouth, going against the settlers' promises.

When Captain Benjamin Church was ordered to safely bring a train of carts to Major Bradford in Taunton.

Upon delivering the train Church was notified that the important native captain Tishpaquine was in the area, and he led an attack against him.