The Cumberland Homesteads Historic District, located on the Cumberland Plateau in East Tennessee, is home to one of the first and largest Homesteads projects attempted during the New Deal era. Although the settlement did not succeed in its original objective, the history of the Cumberland Homesteads has become a valued foundation of the local community, which in turn strives to protect the legacy of the Cumberland Homesteads Tower. To preserve the integrity of the structure as well as the historical integrity of the landscape, the Cumberland Homesteads Tower Association sought to date and potentially remove trees that were not present during the period of significance (prior to 1938). The majority of the trees in close proximity to the Tower were identified as Eastern hemlock (Tsuga canadensis (L.) Carrière) and 15 trees total were sampled. Additionally, three post oak (Quercus stellata Wangenh.) trees were sampled, which are located in a historic ‘triangle’ across the highway from the Tower that had been targeted for removal. Samples were successfully dated, and approximately half of the hemlock were confirmed to have been planted after the construction of the Homesteads Tower. Additionally, post oaks analyzed near the Tower were dated back to the early 1800s, which motivated their protection in the midst of a road project threatening their survival.