By 1844, most all goods and farm products produced in the hill counties east of today’s Greenwood were transported overland to the nearest riverport. However, movement of those items was hard and time consuming because of the lack of a good road system. The work involved in transporting goods and crops across the Delta “swamp” was especially hard. During the wet season, all roads across the Delta were all but impassable. Thus, Titus Howard at Greenwood and Greenwood Leflore at Point Leflore recognized early that the winner of the rivalry between the two riverport towns would be won by the town that was able to develop a good roadway from the hills.
The need to develop a better means for transporting farm products and goods to and from the hills was no new idea.
As early as January of 1836, a group of Williams Landing businessmen, headed by William Gillespie, secured the approval of the Mississippi legislature to construct a railroad from Leflore Town (located at the foot of Valley Hill) westward to “some point on the Yazoo River.” However, the promoters of the railroad were not able to raise the capital needed to build this railroad, leaving only overland travel.
Greenwood Leflore was the first to try to seize the advantage by building a new road from the hills to Point Leflore. Not long after he established his town, Leflore invested $75,000 ($2.5 Million today) to build such a road. According to a report of J. W. S. Merrill of Carroll County, Leflore first built a levee or causeway 10 to 12 feet wide as a roadbed, which he built using his own plantation hands and slaves. Once the roadbed was completed, Leflore topped the road with coal, which was then burned. The residue left by the burnt coal “macadamized” to provide a cover over the top of the roadbed. This layer was reported to be 12 to 15 inches deep, which according to Merrill, made for a splendid road for heavily loaded wagons in dry weather. In wet weather, however, wagon wheels cut through the surface, and it was not long before the road was impassible.
In 1851 in a move aimed at retaking the trade route to the hills, businessmen in the town of Greenwood charted a company to build and operate a plank road to the hills.
A plank road would have had a surface of big wooden planks laid side-by-side but perpendicular to the direction of the road. Heavier wooden beams or logs called “stringers” were placed under the planks. The idea being to avoid mud and ruts. This road was laid out along a line eastward towards the hills with toll gates on each end. Should any man refused to pay or attempt to evade paying, he was to be penalized $10.00 for each offense. The road was to be fifteen feet wide and was to have “turning out places so that wagons could pass each other safely.” Its elevation along the entire route was to be above the “high water mark.” This new plank road would later become known as Carrollton Avenue. According to Merrill, Greenwood Leflore’s coal-surfaced road did not hold up and soon became dilapidated, and both new and old customers chose to use the new plank road from the hills to the town of Greenwood. It was not long before it became evident that Leflore’s riverport of Point Leflore would succumb to Howard’s town of Greenwood. One can only imagine that Titus Howard looked with satisfaction at the decline and later abandonment of Point Leflore. While the Great Chief Greenwood Leflore had warned Howard that he would kill Howard’s town, it was Point Leflore that jointed Mississippi’s list of extinct towns. However, Greenwood would soon face another rival as the Mississippi Central Railroad through the hills would soon provide a new and faster means for transporting the hill regions crops and goods.
