Henagar was named for one of its first settlers, George Henegar, who helped to obtain the post office which was given his name, though spelled differently. James N. Moore was actually the first settler to live in what is now Henagar, arriving around 1855.

Strawberry pickers at Hershell and Sherman Crye's Henagar farm about 1960.

The early citizens of Henagar got their mail at Pea Ridge, some four miles away under the stairs of the log cabin home ofJohnson Jones, built in 1852. Johnson Jones was the Postmaster and Justice of the Peace and his cabin now resides in Henagar Park.

On July 19, 1878, the Henagar Post Office was established and James N. Moore received appointment as the first postmaster. The post office was located in six different houses and served by six different postmasters before the first postmistress, Mary Marjorie Hope, was appointed in 1963 and a modern building constructed.

The Methodist Church was organized in 1873 by the Reverend Jimmie Cox. Services were first held in an old school building near the present location of the old Concord Church. The Methodists completed a log church on June 24, 1880, where the Henagar Cemetery is now. The church was built on land deeded by James E. and Margaret Howard and known as Howard's Chapel. A new church was built where the present one stands in 1907 after J.M. and Sarah Moore donated the land. The new church was called Henagar Methodist Episcopal Church South until 1939 when it became Henagar Methodist Church. In 1913, the Reverend Mack Frost organized the Baptish Church in the Methodist building and the Reverend Charlie Starkey served as the first pastor. They continued to hold services there until 1917 when they erected a building on the site of the present Baptist Church.

In the early 1900's Henagar served as an outstanding educational center with Professor A.H. Mathes running his School of Preparation. The large dormitory and the school building were destroyed in 1910 and a normal school was begun in 1911. The first community school stood where the Big M Supermarket is now located. Later a large two-story building was erected where the present school stands. Eleven grades were taught in this school, which was destroyed by fire in 1937. The present building was constructed by W.P.A workers.

Dr. M.W. Hawkins came to Henagar in 1910 as the first dentist. Dr. J.E. Howard, the first medical doctor in Henagar, was followed by Dr. Eugene Smith. Next was Dr. J.B. Phillips, who bought the first Model T Ford to be used in this area. Dr. Cecil Vaughn built the first medical clinic. After his death in 1942, the clinic was operated by Dr. A.W. Graves.

In 1938 the first bus company on Sand Mountain, the Northeast Alabama Bus Company, was opened at Henagar. Owned and operated by W.M. Beck and James Stoner, this business was a great help to people of the area at a time when there were few cars.

The first cotton gin in Henagar, located near the creek south of the cemetery, was owned by a Mr. Mattox. John and Jim Kerby owned and operated the first grist mill. The first Notary Public was George L. Hicks, who took care of many simple legal matters.

The oldest landmark in Henagar is the house built in 1873 by Jim McGuffy. Now known as the old Hawkins home, it was bought in 1910 by Dr. W.M. Hawkins and is now owned by his daughter, Miss Hope Hawkins.