We compared the relative frequencies of witness trees in historical deeds to the relative frequencies of tree species found in the present forests. Changes in relative frequencies of the five dominant tree species were noted in all ecological subsections, although all species found in the past forests are represented in the present. The greatest changes across the study area were a decrease in the representation of white oak and an increase in red maple. The changes in representation by functional groups show a trend toward loss of fire-adapted species of intermediate shade intolerance with associated gains in species of high shade tolerance. Current FIA data on the species composition of trees in the sapling and seedlings size-classes indicate that the trend of reduced of oak species frequency is likely to continue into the near future. This gradual conversion from oak-dominated overstories to maple-dominated understories is a regional trend. Our findings echo a paradox found in the northeastern United States where after 400 years of land use change, forest cover has largely recovered but relative species composition has been transformed. This paradox may add to the difficulty in designing strategies and treatments for ecosystem restoration. However, as we have shown, the changes can be quantified and placed in an ecological context as support for restoration actions.