We identified prolonged dry (or drought) events during the 1777 to 1869 interval that were depicted in Native American annual pictographic records (winter counts) from several documents for a retrospective analysis with supplementary data and information. Based on available information related to the keeper (author) of the winter count, we approximated the locations of the drought episodes. Based on the locational information, we retrieved and reviewed historical temperature and precipitation data observed at US Army forts during the time interval of the winter count–documented drought episodes. Additionally, we examined Palmer Drought Severity Index data from the North American Drought Atlas, which includes annual drought estimates reconstructed from tree-ring chronologies, for the years and location of the documented droughts. We spatially and temporally compared the Native American drought-related winter counts to the available weather, drought information, and other ancillary information in an effort to cross-validate these relatively sparse and disparate historical climate records. Generally, we found the Native American observations of prolonged dry intervals were in agreement with other observations or available documentation. Thus, winter count observations of other climate-related events may provide an additional source of information for other historic climate analyses.