He was born May 18, 1830, in Virginia. There is a strong probability he was a slave. His parents and other siblings are not known.

Rev. John Henry Winn, Sr. blazed a trail circa 1870 and then led 14 Families in 1872 from Hogeye in Bastrop County, Texas to what is now known as St. John Colony, Texas, located in both Caldwell and Bastrop Counties. Initially, St. John was called Winn Colony, but later changed to St. John Colony after John, Sr. organized St. John Regular Baptist Church. Additionally, in Austin, Texas, the Travis County Association changed its name to St. John Regular Baptist Association in honor of John Winn, Sr.

Rev. Winn, Sr. was a Circuit Preacher who organized St. John Regular Baptist Church, Webberville Baptist Church, Pear Valley Baptist Church, and Antioch Baptist Church.

He was amongst the visionary ministers who, in 1867, divided Texas to preach the gospel of Christ to the newly emancipated slaves. They organized four Christian Associations: Guadalupe Baptist Association, Lincoln Baptist Association, Mt. Zion Baptist Association, and the Travis County Association .

John Winn served the Travis County Association as Vice-Moderator under the leadership of the Rev. Jacob Fontaine, the first Moderator, beginning in 1868. The churches he Pastored also joined the Travis County Association. John Winn, Sr eventually ascended to the role of Moderator (est 1872 – 1879) and spread the gospel throughout the region. Equipped with a wagon and oxen, Rev. John Winn spread the news of the Travis County Association and its vision for Freedmen from 80 miles East to West and 75 miles North to South.

The places were as follows:

(Travis County ) Austin, Bluff Spring, Del Valle, Garfield, Giddings, and Manchaca.

(Bastrop County) Bastrop, Cedar Creek, Elgin, Giddings, Hornsby Bend, Jeddo, Littig, Manor, McDuff, Paige, Rosanky, Smithville and Webberville

( Williamson County ) Taylor, Upton, Coxville, Round Rock, Hutto, and Fiskville

(Caldwell County ) Winn’s Colony, Makieville, and Waelder

(Fayette County), Winchester and LaGrange

As you can see, John Winn Sr. did such a mammoth job of spreading the word of Freedom, Faith and Family throughout the region that the members favored changing the name of the Association to St. John Regular Missionary Baptist Association. Although the name changed, the association continued on wheels.

John Winn, Sr., and Jane Allen married circa 1862. According to the 1910 census, Jane said she had fifteen children, and nine were still living: Martha, Abraham, John Jr, Thomas, Emma, Spurgeon, Anthony, Lee, and George. Four went on to become Ministers, two Deacons, and two Missionaries. Jane might be the sister of Calvin Allen, Sr.

Rev. John Winn, Sr. died October 13, 1888, in Lytton Springs, Caldwell County, Texas. He is buried in St. John Colony Cemetery.

Mary Williams-Ellison – great,great grand-daughter of Rev. John Henry Winn, Sr

Dr. Virginia Stewart Miller, great, great grand-daughter of Trailblazers Rev. Calvin Allen and Josiah Hill.