Isaac Cummings came from England to this country in October, 1635. The first mention of his name in Middlesex County records is an entry made by the town clerk of Watertown as receiving a grant of 35 acres in the earliest general land grants in 1636 called the "Great Dividends". Also, a record exists made by the Town Clerk of Ipswich, showing that he owned a planting lot near Reedy marsh, in that town, previous to July 25, 1638.

On the 9th of the second month (April) of 1639, he also owned a house lot in Ipswich village on the street called the East End, next to the lot owned by Rev. Nathaniel Rogers. He was a commoner in 1639, and the same year sold 7 acres of land near the highway leading to Jeffrey's Neck to Andrew Hodges. He also possessed, in 1639, land adjoining John Winthrop and William Goodhue, the farm being partly in Ipswich and partly in Topsfield. He was a proprietor in Watertown in 1642, and at Topsfield afterward, where he was one of 30 commoners.

As an Ipswich commoner, he was one of those "that have the right of commonage there the last of the last month (Feb), 1641", and was made a freeman in Watertown May 18, 1642. On the first day of the second month (April), 1652,Isaac Cummings, for 30 pounds, bought of Samuel Symonds, 150 acres of land, "being the North-east corner of his farm called Ollivers". This lot of land was in Topsfield and bounded on the west and north-west by land lately of John Winthrop, on the south and west by land of Francis Peabody, and on the south by land of Daniel Clark.

The farm began at what is known as the Hobbs-Bell place, and continued down both sides of the brook, then called "Winthropps", to what is now called Howlett's Brook, one hundred acres lying on the westerly side and fifty acres on the easterly side, probably joining other land belonging to him.

There are several court records of him: