The state of Kentucky and the North Carolina (NC) Piedmont represent large spatial gaps in public tree-ring datasets. For Kentucky, there are only four unique sites currently represented on the International Tree-Ring Data Bank. For North Carolina, only 26 unique sites are represented; less than 12 were collected from sites east of the Appalachian Mountains, and only seven are from Piedmont sites. Like other eastern states, Kentucky and North Carolina old-growth forests were removed for logging and agriculture during settler colonization of the states. Dendroarchaeological data are one way to fill these gaps, and provide important information on area history, but also on climate, ecology, and human-environment interactions. A long-term objective of the University of Louisville Tree-Ring Laboratory is to develop an improved and spatially extended tree-ring network across the southeast US using dendroarchaeological data. This work is ongoing; so far, over 20 structures have been sampled through spring 2022. Multiple tree species are represented by these data, including shortleaf pine, white oak, tulip poplar, white ash, eastern hemlock, black walnut, and American beech. In this presentation, I share the most up-to-date findings from ongoing efforts and story the successes and struggles of dendroarchaeological work in a region lacking abundant and long-lived reference chronologies. I also highlight observations of traits so far unique in my own studies to Kentucky and NC Piedmont structures, which shed light on timber choices and workmanship, and in one case, provenancing of materials.