We evaluated 50‐year‐old bottomland forests in southwestern Kentucky restored from agriculture by planting and natural regeneration in terms of their development toward mature forests. We described and compared the structure and composition of the plant communities of three stands of each type (planted, naturally regenerated, and mature). Increment cores were analyzed to reconstruct developmental trends. Future trends were predicted from analyses of the midstory and understory composition. Both planting and natural regeneration adequately replaced the structural attributes of the historical bottomland forest. The existing structural differences are expected to diminish over time. Neither regeneration method replaced the wildlife value of the mature bottomland forests due to insufficient establishment and subsequent ingrowth of heavy mast species (particularly oaks and hickories). There was evidence that the understory species compositions of the restored forest types were similar to that of the mature stand type. All forests, including the mature stands, appeared to be succeeding from hydric to mesic species compositions as a result of human‐altered hydrology and natural floodplain processes. We speculate that the historical bottomland species composition will probably not persist on any of the study sites in the long term.