John Crooke, born February 10, 1766, commonly called Major Crooke, was born in St. Mary County, Maryland. He enlisted while yet young in the Revolutionary war , and was with Washington at the capture of Lord Cornwallis at the siege of Yorktown, Virginia. He was married to Anna D. Reeves, the 5th January 1786. John Crooke studied mathematics pretty thoroughly; could master the arithmetic, and made one (book) himself. He understood navigation; could box the compass; made almanacs; and could count the eclipses of the Sun and the Moon; and in one almanac he left a little space along the margin, and late in May, he put down "Frost" and at the Battalion Muster the day before his frost, they laughed at him about his prediction; Says he: hold, wait and see. That evening a cloud came up from the North, rained a good shower, and a cleared off cold, and sure enough in the morning was a white frost. He was thenceforth put down as an almanac maker, and a sure prophet. Major John Crooke with his wife, Anna D., and father, Osias Crooke, and two more brothers, Hezekiah Crooke and Absalom Crooke, immigrated from Virginia to Kentucky, in the year 1789. At that time many surveyors were in Kentucky, then part of Virginia, surveying out the military claims of the Revolutionary soldiers; the soldiers were all allowed a preemption of 1,000 acres of land and a homestead of 400 acre, generally laid out together.

Madison was made a county, still of Virginia, in 1785, and James French was her first county surveyor, and held the office for eight years. He held his office from appointment in Virginia. John Crooke was one of his deputies. John Crooke was the first surveyor elected to the office after the establishment of the state, by the magistrates of the county. Major John Crooke made many tables of numbers such as tables of logarithms, and the traverse table, and more than thirty maps of the different states and territories, the United States, Mexico, etc; and laid off all the counties in good colors all with his quill-pen. He made several maps of Madison county, and made connected plats of all the land in the county. He surveyed most of the lands in the early litigations in Madison and much in other counties. When he first became surveyor, Madison county extended to the Virginia line, on the south side of the Kentucky River. He had many deputies, and some of their names were James Kincaid, Richard Smith, David Williams, Jones Hoy, George Walker, James M'Cormick, Daniel Boone, William O'Rear, Thomas Mosely, Thomas Campbell, Wallace Estill, Joseph Barnett, James Anderson, Irvine Anderson, John R. Crooke, Kiah Crooke, and others.