In 1629 a 20-year-old cartographer, William Wood, arrived in the colony at Sagus (Lynn). Under the Council of New England Company of John Endecott's charter, he began mapping the northern shore of Massachusetts Bay, rivers, tributaries and noted existing native and immigrant settlements. In his published book New England Prospect in 1634, Wood states that in his opinion "Agawam (Ipswich) is the best place but one, which is Merrimack, where the river is twenty leagues navigable". Wood's map marks Pemtuckett (Haverhill) as a settlement. Twenty-six miles up river from the ocean is the "great water" falls Cochichawicke, called by the natives, the area that would become the plantation town of Andover.
Gov. John Winthrop arrived in 1630 with his "Massachusetts Bay Company Charter" granted by King Charles. Puritan Winthrop represented interests in England concerned with governing the new plantation, but also the economic possibilities in the fur trade market of his financial backers, including the Earl of Lincoln. Two of the most valuable trade items for the local Indian populations were beaver pelts and land. Winthrop wasted little time in encouraging interior settlements as nearly 25 townships had been settled since Plimouth Plantation.
The first Legislative act concerning Andover was held at the General Court in New Town (Boston) on March 4, 1634. It ordered that all the land of the place called Cochchichewicke be reserved for an Inland Plantation. To entice settlement of the nearly 70 square miles of land the Court promised immunity from all taxes, levies, public charges and services for three years. The only obligation attached to the order was service to the military. John Winthrop, William Bellingham, and William Coddington, Esq., were chosen as a committee to grant license to anyone that they think met the requirements to inhabit there. Only those who swore allegiance to the covenant were granted charters. The power to select a population of virtuous and pious families rested solely with the committee.
John Woodbridge and Simon Bradstreet had been selected to settle Cochchicewicke in 1640 but the settlement stalled as a dispute over the boundary with Rowley ensued. The Court ruled against Rowley's claim and the plantation began in 1643 but it would be two years before Woodbridge would be ordained pastor in October 1645.
Seven months later at the General Court at Boston, "on the 6th, 3d month, 1646," Chief Cutshamache, acknowledged that he had sold for the sum of ¬£6 and a coat, "to Mr. John Woodbridge, in Behalf of the Inhabitants of Cochicawick, now called Andover, all his Rights, Interests, and Privilege in the Land... provided that the Indian called Roger, and his company, may have Liberty to take Alewives in Cochicawick River, for their own Eating; but if they either spoil or steal any Corn, or other Fruit to a Considerable Value of the Inhabitants there, this Liberty of taking Fish shall forever cease. And the said Roger is still to Enjoy four Acres of Ground where now he plants."
Andover was now an incorporated village plantation and laid out the first village center on Academy Road in North Andover center. Nothing is known about the Indian Roger and whether the agreement of the sale was kept. Only Roger's Brook, that runs from the top of Summer Street to the Shawsheen River, pays tribute to him and his company of Native Americans near Cochicawick.