The American chestnut (Castanea dentata) was once widespread in eastern North America and an ecologically important hardwood tree of deciduous forest communities prior to its near-eradication by chestnut blight (Cryphonectria parasitica). Remnant populations occur across much of its historical range, especially in older forests of the Appalachians and northeastern U.S. However, broad swaths of the southwestern portion of the species’ historical range remain poorly documented, potentially limiting the representation of genetic variation important for local adaptation in restoration efforts. Ongoing discovery and life-history characterization efforts for remnant C. dentata remains a priority to better understand the distribution and ecological status of this once important species, while identifying potential genetic sources of locally adapted or blight resistant trees. Here, we report the discovery of 22 C. dentata at four sites in southwestern Tennessee, adding novel observations that extend the range of known extant occurrences to the extreme western edge of the historical distribution in Fayette County. These observations include potentially reproductive individuals that should be revisited to assess reproductive and blight status, and that should be evaluated for current germplasm collection and restoration efforts.