Henry B. Woolsey was a farmer and nurseryman of Osage Township, three miles southeast of Bentonville, was a native of Hempstead County, Ark., born in 1830, and was the son of Samuel and Matilda (Thompson) Woolsey. HIs father was a Kentuckian by birth, the same occurring in 1787, and was also married in that state. In 1808 he moved to New Madrid, Mo., from there to Hempstead County, Ark., in 1811. and in 1829 he moved to Washington County, of the same state, where he passed the last years of his life. He was one of the first settlers of both Hempstead and Washington Counties, and during his first year's residence in the former county his principal diet was buffalo meat. He was a great hunter, a skillful marksman, and was fond of the rude life of the pioneer. He was a soldier in the War of 1812, and fought the Creek Indians in the State of Kentucky. His father, John Woolsey, was born in New York State, was in the Revolutionary War, also the War of 1812, and in the latter war he and his son, Samuel, enlisted in the same company and regiment, and were at the battle of New Orleans. John Woolsey died in 1839, at the age of one hundred and five years. Samuel Woolsey's wife, Matilda Thompson, was born in Kentucky in 1791, and died in 1877.She was the mother of thirteen children, Henry B. being the tenth child.
Henry B. was but an infant when his parents moved to Washington County, and here he was reared and educated. He worked on the old home place, which consisted of 200 acres, four miles west of the county seat, until twenty-four years of age, and in 1854 married Miss Margaret Neale, who was born in Boone County, Mo., in 1834. To their marriage were born six children.
Mr. Woolsey resided in Washington County, Ark., until 1857, when he became a resident of Bentonville, Ark., and worked in a wagon-shop. In 1861 he purchased eighty acres of land in Section 33, Township 20, Range 30, where he located and since resided. About 1866, he started a nursery on a small scale, and continued to increase his stock, when his son-in-law Alvin Dickson, became a partner, and they devoted their time and attention to this work. They had in 1889 at least 300,000 trees, in fine growing order. Mr. Woolsey was one of the old settlers, and was a man well respected by his friends and acquaintances. He was a Democrat in politics, and Mrs. Woolsey was a member of the Methodist Episcopal Church South. Mr. Woolsey passed away on August 9, 1909, and is buried in the Bentonville Cemetery.
Adapted from Goodspeed - History of Benton County 1889