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In the years 1708-9 John and his younger brother Isaac, and cousin Jonathan made several trips south into the unsettled portions of the Colony of Connecticut. They were attracted to the opportunities in Killingly Township in the northeast corner of Windham County, Connecticut.

This County was owned by the Colony itself, rather than by individual or corporate grantees. Eager to attract settlement, the Colony had laid out Killingly Township in 1708, established certain minimum settlement requirements and granted an option for £40 to Joseph and James Leavens and a few others to develop the area. John and Isaac bought the mill on the Asawaga or "Five Mile" River from James Leavens, with Isaac remaining as one of the original 30 settlers. Jonathan was one of the original 30 also, but sold out in 1710. John's only interest at that time was the mill, and he returned to the family in Cambridge Farms (now Lexington) to make arrangements to move south. In 1713 John moved the family to Killingly, Connecticut, in our family's first major move since 1650. He paid James Leavens £120 for a 200 acre farm next to Isaac. When you recall that the option on the whole area had cost only £40 four years previously, the price of triple that for just one farm indicates the values to be had in land promotion.

The Leavens boys were instrumental in getting the Cutlers to move to Killingly, both James and Joseph Leavens would become ancestors of ours, and for the next 115 years the Cutlers and Leavens would be intimately associated, so some background should be given.

The original settler, John Leavens, came from Oxford, England in 1632, settled in Roxbury, near Boston and became a freeman in 1634. Of his three sons, one was killed in King Philips War, one died in the army unmarried, leaving as sole heir John² Leavens who later moved to Stratford where he married Elizabeth Preston and later became one of the original grantees of Woodstock, Massachusetts (which later was made part of Connecticut.) These people often would go down the Quinebaug River to the future site of Killingly to cut wood and gather game. John² Leavens' four sons James³, Joseph³, Peter³ and Benjamin³ moved to Killingly, with James and Joseph as the active developers.

James³ Leavens was a most enterprising man. Even as a boy he had collected turpentine and other materials, selling them to men in the nearby settlements. From this he naturally began to trade land grants and businesses such as mills in later years. He married Mary Chamberlain of Woodstock. His son John⁴ became a man of the greatest prominence in later years, and his daughter Elizabeth⁴ married our Timothy⁴ Cutler in 1733.

Joseph³ Leavens was the leading citizen of Killingly for many years, being Justice of the Peace for the County most of the time and often being called upon to settle the affairs of neighboring communities. He was known as "old one-thumb" most of his life, since he had been bitten on the thumb by a rattlesnake when he was working in the woods alone at the age of seventeen, and knowing that he had to act quickly, simply chopped off the thumb with his axe. Though he was a kind and generous person renowned for fairness, he was such a dignified and imposing man that the entire community lived in awe of him and he is said to have terrified the young children.

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