"Our Heritage"
Mt. Olive Tribune
By Claude Moore
Friday, July 9, 1993

I have known of the Winn Family of Dudley and Mount Olive all my life, but only recently have I met Henry Winn of Mount Olive, who has collected much data on this family and their forebears.

I am relying on his data as a reliablle source. I have not had the time to check the land records in Duplin, nor have I checked the Census records. The Winns are widely connected with the Simmons, Brewington, Jacobs, and Carter families.

Prior to the War Between the States, these families were free, and when the first census was taken in 1790 they were listed as "free persons of color" and sometimes called "free issue." They intermarried among themselves since they were forbidden by law to intermarry with slaves. Many of them undoubtedly had some Indian blood as well as African blood. Some of these families owned land, and the Winn family not only owned large tracts of land but they owned some slaves. The Census of 1860 lists these families as Mulattoes.

The first known member of the Winn Family was Adam Winn who originally lived in Duplin County and is believed to have been descended from the Waccamaw Indians. He moved to Wayne County and bought several tracts of land including land on which the Town of Mount Olive is located. He sold land 1836-1840 for the building of the Wilmington & Raleigh Railroad, later known as the Wilmington and Weldon Railroad.

Adam Winn had five sons: Adam, Gray, Washington, Charles, and Levi. Adam Winn Jr. married and had five sons: William, Marshall, John, Woodward, and Woodley. Charles Winn (1817) married America and had the following children: William, Meria, Churchill, Margaret, Levi, Mary, Frances, Lebyet, Wyatt, and Charles.

Gray Winn (1818-1850) married and had the following children: Betsey, Edward, Eliza, Penny, Annie, and Washington Frank. Levi Winn married twice and had the following children: Henry, David, Pinkney, George, Charles, Mary, Martha, John, Elizabeth, Susan, and Levi. Washington Winn (born 1820) married first Larky of Sampson County and second, Temperance Brewington and their children were: Aaron, Levi, Apoly, James, Giles, George, Aubrey, Elizabeth, Lesley, Mary, Della, and Louella. Washington, Charles, and Levi Winn were farmers and also worked as carpenters and blacksmiths.

After the War Between the States, the Winns and their connections were able to vote, and they became members of the Republican Party. Washington Winn was a Wayne County commissioner from 1872-74. He was postmaster of Mount Olive from 1881 to 1885. Levi was a justice of the peace in 1870. When the town of Dudley was incorporated in 1897, Charles W. Winn was one of the first commissioners.

The land on which the Winn Chapel Missionary Baptist Church was built in 1878 in Mount Olive was given by Washington Winn by deed in 1875 and the first pastor was the Rev. Washington Winn. In 1880, the first school for black people was established in Mount Olive with E. E. Smith as the first principal. Susie Winn was one of the early teachers, and in 1896, Cora Winn joined the faculty.

There are literally thousands of descendants of Adam Winn now living in the United States. Some identify as African-Americans, others as Indians and a few identify as White.

Henry Winn, now 81, was born in Wayne County and he attended A & T College three years. In 1935, he moved to Connecticut and then Massachusetts. He served in the U.S. Army 1941-1945. After the war, he was a successful business man in Washington, D.C. and now living in Mount Olive. He is a member of the First Congregation Church of Dudley.

Mount Olive Tribune
September 7, 1979
Volume 76 – Number 44 – Section B
By John Baxton Flowers III

The Winn Family

The Winn family is one of the most interesting in the area. In 1836 Ginny Winn purchased a hundred acres of land from Ezekiel Norris in the lower part of Wayne. This is the first land transaction by Winns in Wayne County, though John Kornegay of Duplin County deeded Adam Winn, also of Duplin, land on the northeast “precosin” (swamp) on September 18, 1834. This land ran into Wayne County at one point near present-day Mount Olive.

In the 1850 census the Winn family is listed as “mulatto”, but in the 1860 census they were listed as “black”. The Winn family were free blacks from Duplin County who had received their freedom prior to 1834. The Artis Simmons and Greenfield families of Mount Olive were also free blacks, according to the 1860 census.

Adam Winn was himself a slave owner, for in April 1849 he borrowed money from Benjamin Oliver of Duplin, and put up three slaves, Bethana, Martha and Oliver, as security, along with 133 acres of land. The Winns did business with the most prominent and respected white families, and through the years have generally been considered the most outstanding family of their race in the area. They have produced farmers, school teachers and tradesmen and have been leaders in the black community of Mount Olive. Adam Winn who was also one of the first magistrates of Mount Olive, had sons, William, Charles and Levi. Charles and Levi were blacksmiths, the first to be located in the village of Mount Olive. Levi Winn owned land west of the railroad which was later purchased by Dr. Roberts, and transferred in 1854 to William W. Loftin and Dr. Benjamin Franklin Cobb. William and Charles Winn also owned land in the Mount Olive area.