We used dendrochronology and vegetation sampling to examine climatic response and stand dynamics at two slope positions (350 m asl and 520 m asl) on No Business Mountain in the southwestern Piedmont of Virginia. Modeling plant response to climate change requires an understanding of the influence of small-scale environmental change. We sampled vegetation and developed pitch pine and Virginia pine tree-ring chronologies from the midslope and the mountaintop. A higher species richness and more hickory and black gum were found at the mountaintop. Significant correlations existed between tree-ring growth and temperature in the late fall and precipitation from the prior years’ summer months; however, the same dendroclimatological response existed for both species at both slope postions. According to the dendroecological analysis, pitch pine entered the sites after agricultural abandonment in the early 1900s, and Virginia pine entered the sites following a release event in the 1940s. Recently, the pine stands on No Business Mountain have converted to an oak stand at midslope and an oak-hickory stand on the mountaintop. Microenvironmental differences between the two slope positions at No Business Mountain influenced vegetation composition but did not result in different dendroclimatological responses. These results imply that small scale environmental differences other than climate (soils and land use history, in this case) may be more important to vegetation distribution; therefore, it may not be necessary to include plant response to small-scale climatic changes in climate change-vegetation response models.