The dichotomy of the earliest ecosystems into deltaic and floodplain forests was a long-standing view in paleobotany. The morphological traits such as nonbranching rootlets, bifurcating rhizomes, and bulbous bases of the primitive trees such as Eospermatopteris and lycopsids were considered adaptations to the lowland deltaic environments. In contrast, the traits of Archaeopteris trees such as wood, hierarchical branching networks of roots, and true leaves are an adaptation to the upland floodplain environments. The discovery of the Town of Cairo Highway Department (TCHD) fossil site in Upstate New York, where all major clades occupied a floodplain environment casts doubt on the validity of the environmental partition by the earliest trees at the higher taxonomic levels. This study aims to test the hypothesis of the environmental partition at the local scale by reconstructing the fossilized forest-floor landscape, the changes in the landscape over time, and the distribution patterns of the trees along the local environmental gradient at the TCHD site. To reconstruct the fossilized forest floor and to determine the environmental variations at the local scale, seven parallel cross-sections were drawn from south to north at THCH. The outcrop at the quarry floor measured 300 m in the north-south, and varied around 100–150 m in east-west direction. Primary sedimentary structures, the thickness of the sedimentary deposits that formed the forest floor and the surrounding quarry walls, paleosol features, and mega-fossils were measured, recorded, described, and mapped. Up to 3 meters deep drill-cores were extracted from the forest floor. The data was used to correlate the sedimentary deposits, and reconstruct the preserved landscape. Three dominant landscape features including an abandoned channel, an old-grown forest, and a local depression were recognized. These landscape features influenced greatly the pattern of local drainage, slope-gradients, patterns and durations of seasonal water pooling, paleosol developments, fossil distribution, and depositional environments. There is no evidence of environmental partitioning by trees at higher taxonomic levels at the local scale. The size and morphology of the root systems didn’t determine the distribution of the trees along the local environmental gradient such as drainage patterns but played important roles in tree stabilization. Forests would go through self-thinning as they matured. Upon comparison, it was found that the forests in unstable environments showed greater resiliency compared to forests established in the stable environments.