The Great Wepawaug Chief

Imagine the small coastal town of Milford, Connecticut inhabited only by Native Americans. The Wepawaug tribe, a branch of the larger Paugasset tribe resided in what is now Milford and Orange. Ansantawae the chief or sachem of the Wepawaug Indians along with his tribal council controlled the Indian village. Life was lived simply in small wigwams made of sticks and leaves, currency did not exist, nature provided much of their food, and English settlers had not set foot upon the land now Milford as of 1637. This all changed during the reign of King Charles I when increasing numbers of English people migrated to New England because they no longer accepted of the Church of England and were persecuted for their non-conformity.
The Wepawaug tribe lived in present day Milford sites that were full of resources, mainly along the shoreline. Villages were set up at Charles Island, Indian Point presently (Gulf Beach), Poconoe Point (presently Laurel Beach), the Wepawaug River and Oyster River. Their seaside location made Ansantawae’s tribe largely dependent on fishing, especially shellfish such as oysters and clams that flooded the shoreline. Milford residents still use the Sound shore as an important and abundant resource. Large heaps of shells found along Milford’s coast give evidence of the Indians reliance on the water and its life.

Nevertheless Ansantawae’s tribe did not rely solely on Long Island Sound as a resource, as land was plentiful too. Milford’s wildlife proved bountiful with pigeons, quails, turkeys, partridges, cranes, geese, ducks and beavers to hunt for food, skins, and feathers. Though the Wepawaugs did not largely depend on agriculture, they were able to grow maize, tobacco and beans to support themselves. They also were known for gathering strawberries, blueberries and blackberries. Ansantawae and his tribe were successful in drawing a healthful diet from the bountiful lands around the Wepawaug.
In May of 1637 the “Hector” sailed from London to Boston carrying John Davenport, Theophilus Eaton and others from London. It was followed by another ship weeks later carrying many of the original English settlers of Milford, including Robert Treat, John Sherman, Thomas Tibbals, John Fletcher and led by Peter Prudden. Although they remained in the Massachusetts Bay Colony for almost a year, Davenport and Prudden had from the start desired to establish their own colony. In August 1637 on an expedition during the Pequot War, the region at the mouth of the Quinnipiac River in Connecticut was discovered and marked as a potential location for settlement. Davenport and company decided this was the place to settle their colony which would later become present day New Haven. After the Pequot war, as the Connecticut and Massachusetts militia began to pursue the remnants of the Pequot tribe along the Connecticut coast, Sergeant Thomas Tibbals noticed the region above the mouth of the Wepawaug River. Using an old Indian trail that is today the Boston Post Road, Tibbals and his troops explored the area that is today Milford and appraised it as an ideal spot for settlement.