He had taken an active and prominent role in organizing the town of Rehoboth. His services to the town were recognized at a public meeting held July 12, 1644. The town ordering that he "should have division in all lands of Seakunk, for one hundred and fifty three pounds, besides what he is to have for his own proportion, and that in way of consideration for the pains and charges he hath been at for setting off this plantation." In 1645, he was proposed for freemanship at the General Court in Plymouth, but was not admitted until 1648.
The first act of the General Assembly of Connecticut was an order prohibiting all persons from selling firearms and ammunition to the Indians; another act was passed in 1642 "forbidding smiths from doing any work for the Indians, or selling them any instruments or matter made of iron or steel without a license from two magistrates." Various other acts were passed regulating and in some cases prohibiting trade with the Indians.
William, like most of the early planters, traded with the Indians, the records show he was trading at least as far away as Long Island, and may have lived there at some point as well.
On May 5, 1646, the Plymouth Court ordered a Rehoboth constable to arrest William for his part in "an affray made upon Ussamequine and some of his people" he had to post a 20 pound bond. On June 2, 1646 the court ordered that he pay three shillings apiece for the mending of two locks for firearms and the abuse of Ussamequin and in addition, for his breach of imprisonment and fleeing to a foreign government, (probably RI) he was ordered to prison for 14 days without bail or mainprize, and to pay a 6 pound fine for the colony's use.
Looking for a new homestead, he was encouraged by John Winthrop jr. to have a look a Pequot (New London). Finding it lacking in many respects, he headed for home and passed through the Pawcatuck region. This area had all the resources he was looking for. He decided to settle at the head of Wequetequock Cove, the marsh surrounding the area providing hay for his large herd of stock. His friend Roger Williams, encouraged and assisted with his move. His family which consisted of his wife and four sons, Samuel, Nathaniel, John and Elisha and the two wives of his eldest sons, joined him in the summer of 1649. His home stood on the west side of Wequetequock Cove, near the head of tide water.
Having heard of his previous dealings with the natives in Plymouth, the Connecticut General Court issued an order on Nov. 7, 1647, which sent a Constable of Pequet to let William know that they did not like the way he did business with the natives, that they expected him to stop and appear before Capt. Mason or some other River Magistrate to explain himself.
At first William disregarded the order, claiming that his new home was within the jurisdiction of Massachusetts, but acting under the advice and assurances of Mr. Winthrop and other friends at Pequot (New London), he agreed to appear before the authorities of Connecticut General Court at Hartford in March of 1651. There he addressed their questions about his character, trading with the Indians and future plans in the area.
He stated that he had sold all his former property and was planning to settle in the Pequett plantation, but he found it unsuitable in many respects. He had decided to build his house and move his cattle to Wequetequock which was better suited to his needs. When he sold his property in Rehoboth, he all so his tools and could no longer repair gun locks or " making so much as a screw pin."
When asked why it "seemed more than uncomely for a man professing Godliness to withdraw from all public ordinances and Christian society" he said he didn't intend to remain solitary, but intended to "in a short time to procure a competent company of desirable men, for the planting of the place."
The court reluctantly permitted him to remain on condition that he would a bond of 300 pounds not to carry on any unlawful trade with the Indians, and giving him until the following September to furnish them with the names of the persons who would settle at Pawcatuck before winter, for their approval.
William went to Hartford to get a title for the land he was occupying, but the planters of Pequot, Mr. Winthrop and the deputies from Pequot preferred that he settle in that settlement rather than create a new town. An agreement was made that if he agreed to become part of Pequot they would grant him title to his land. Since his lands were out side the bounds of that town the court "on request" extend the bounds of the settlement to Pawcatuck River, so as to include his land. In November the town gave him a house lot at Pequot, which he never occupied.
In January, 1652, a large tract of land was given to him by the town of Pequot, which was later enlarged to between two and three thousand acres. William succeeded planting his new town with enough "acceptable persons" to satisfy the General Court and the settlement of the town was begun. In 1654, the planters wanted a separation from Pequot for religious, as well as civil reasons. The planters of Pequot were not happy about this. William's settlement was located in a hotly contested border area.
At about the same time his request for separation occurred, Massachusetts laid claim to the area. This action started a controversy that went before the court of the Commissioners of the United Colonies. The final outcome was decided in 1658, all of the territory east of the Mystic River went to the Massachusetts Colony, to be called Southertown. Then in 1662, it was included in the new charter, and went to the colony of Connecticut. In 1665, the town got a name change from Southertown to Mystic. In 1666, the name changed again, this time to Stonington.
William seems to have been a man great energy and ability, holding positions of trust in the Massachusetts Colony, in addition to being prominent in the settlement of Rehoboth, in the Plymouth Colony. After his homestead at Wequetequock was included in the township of Pequot, he was elected deputy to the General Court at Hartford in 1653-4-5-6, and on one occasion rate-maker or assessor.
In 1658 when the Massachusetts General Court asserted jurisdiction over this town, William along with some others were appointed to manage the business affairs of the town, and one of the Commissioners to end small causes and deal in criminal matters.
He held the office of Townsman (Selectman) until Southertown was annexed to Connecticut, and was the first man elected deputy after the reunion, 1653, '55, ' 57, '64. He succeeded in restoring good relations with the Court which had been seriously damaged by the jurisdictional controversy. After his return he was elected first selectman of the town, and re-elected every year up to the time of his death, which took place June 9, 1667.
William Chesebrough along with Walter Palmer, Thomas Stanton, Thomas Minor, and George Dennison were the founders of Stonington (Southerton) Conn. Their decendants played leading roles in that town.
William and Anna Stevenson had children:
1. MARIE, bapt. Boston, Eng., May 2, 1622, buried June 9, 1622.
2. MARTHA, bapt. Boston, Eng., Sept. 18, 1623, buried Sept. 28, 1623.
3. DAVID, bapt. Boston, Eng., Sept. 9, 1624 (twin), buried Sept. 9, 1624.
4. JONATHAN, bapt. Boston, Eng., Sept. 9, 1624 (twin), d. young.
5. SAMUEL, bapt. Boston, Eng., April 1, 1627, m. Abigail Ingraham.
6. ANDRONICUS, bapt. Boston, Eng., Feb. 6, 1629, d. Feb. 8, 1629.
7. JUNICE, bapt. Boston, Eng. (twin), Feb. 6, 1629, d. Feb. 6, 1629.
8. NATHANIEL, bapt. Boston, Eng., Jan. 28, 1630, m. Hannah Denison.
9. JOHN, bapt. Boston, Mass., Sept. 2, 1632, d. Stonington, Conn., 1660.
10. JABEZ, bapt. Boston, Mass., May 3, 1635, d. young.
11. ELISHA, bapt. Boston, Mass., June 4, 1637, m. Rebecca Palmer.
12. JOSEPH, b. at Braintree (now Quincy), Mass., July 18, 1640, d. young.
See direct line to my NY Terrys
Map of Stonnington with property lines in PDF
Information compiled from The Great Migration begins and History of Stonington Conn.