Henleyfield is located deep in the Piney Woods Region, which meant until the early 1900’s the area was covered with forest made up mostly of gigantic long-leaf yellow pines. Some of these trees were so large three grown men couldn’t reach around them. The dense forest, and the limited tools available to the early settlers for tree removal, meant there were few roads and little open land for farming. In those days, the two roads that crossed the area were the Columbia-Gainesville Road and the old River Road. The Columbia-Gainesville Road was the road settlers traveled on horseback or walked to Gainesville where they bought supplies and got their mail – a trip that took up to a week. This road ran up from the old town of Gainesville on the Pearl River near the Gulf, through what is now Picayune, along what is now Liberty Road and George Wise Road, angled into what is now Highway 43, and twisted and turned on to Columbia along the same route Highway 43 follows today. The old River Road branched off the Columbia- Gainesville Road where Joseph Burks Road is today and followed along the Pearl River Southward. All North and South overland traffic through the area used these two roads. In those days the area was sparsely populated and settlers were self-sufficient, raising free-range livestock and crops to feed their large families. These early settlers were predominately Anglo- Saxon Protestants and some Henleyfield residents today are descendents of those old families.
In the 1880’s the railroad came through Pearl River County and stores and post offices at the railroad spurs in Carriere and McNeill meant area residents could get their mail and supplies closer to home. In the early 1900’s the large timber companies came into the area and harvested the virgin pine trees. During that time railroad dummy-lines for transporting timber to the sawmill crisscrossed Henleyfield, and some of the men of the area felled the large trees, pulled them to the river with teams of oxen, then floated them down the river to the sawmill to sell. With the harvesting of the trees, the land was opened up for farming. Land was cheap, or free if homesteaded, and many of the children of the early settlers set up farmsteads, joined by new residents.
During the beginning of the Twentieth Century, home life was much the same as it had been for the early settlers. Laundry was done at the creek or in a wash pot. Cooking was done on a wood-burning stove. Each family butchered their own meat and preserved it by smoking it in their smokehouse. The ladies made quilts and clothes for the family by hand and on treadle- type sewing machines. And each house had a little house out back. Automobiles started showing up in the 1920’s and 30’s, and by the early 1920’s Henleyfield’s population had grown to the extent a new school for first through twelfth grades replaced the smaller schools in the area.
The 1940’s brought big changes to Henleyfield. With the entrance of the United States in World War II, most of the men of service age went away to war. When they returned, many of them married and settled in Henleyfield. Also, electricity finally reached Henleyfield in the 40’s.
Until the mid-1950’s, when the Picayune Sycamore-8 exchange came to the community, the nearest phone was in Byrd’s Chapel. During the 1950’s and into the 60’s there were three stores in Henleyfield and residents went to the store for bread, milk, nickel soft drinks, penny candy, and the latest news of the community. From the beginning, religious belief played a big role in the lives of Henleyfield residents and nearly every family was affiliated with one of the community churches. When hard times came, neighbors were always on hand to help. One sad occurrence of the 1950’s was the closing of the Henleyfield School due to consolidation of county schools. The kids of the community were now bussed to schools in Pine Grove, Picayune and McNeill.
Almost every family in Henleyfield farmed either as their main source of income or to supplement the salaries from their regular jobs. The 1950’s and 60’s was the era of the tung tree. Most farmland was divided between tung trees, pastureland for livestock, and acreage for raising other crops, including corn and hay for livestock feed. The fruit of the tung tree was harvested in October, and anyone of a certain age who lived in Henleyfield during this time has picked up tung nuts. In the years when the crop was good, the tung oil farmers’ families had a good Christmas. In the years when a late freeze or a hurricane damaged the crop, everyone hoped for a better crop the next year. Families raised gardens and the ladies of the house spent much time in the summer shelling peas and butterbeans and canning a variety of vegetables. Freezers were well stocked with vegetables and meat raised on the family farm, and pantries were stocked with jars of fruit, vegetables, jams, jellies, and pickles that were fit for prizes at any county fair.
In August 1969, Hurricane Camille dealt the area a hard blow, destroying the tung orchards overnight. The era of the tung tree was over. The old tung orchards were cleared, and some land was turned into pasture or used to raise crops such as soybeans, while other land was divided up and sold off. Anyone who lives in Henleyfield today can still see evidence of the old terrace rows, and the descendents of the old tung trees that pop up along fence rows and in the woods to bloom in shades of cream and peach every spring.
Few people in Henleyfield still rely on farming as a living. Most of the old farmers have died off and the farms have been divided among their descendents or sold to new residents. Many other former residents have “moved to town” for convenience and employment opportunities. During the 1970’s, 80’s, 90’s up until today, families from other areas have bought property here and made Henleyfield their home. Most people of working age commute to jobs in the surrounding area, and a large percentage of the current residents are very busy retired folks. Newer residents have been welcomed to the community, and that strong sense of community still exists today.