Warming is a major climate change concern, but the impact of high maximum temperatures depends upon the air’s moisture content. Trends in maximum summertime temperature, moisture, and heat index are tracked over three time periods: 1900–2011, 1950–2011, and 1979–2011; these trends differ notably from annual temperature trends. Trends are emphasized from two CRU datasets (CRUTS3.25 and CRUTS4.01) and two reanalyses (ERA-20C and 20CRv2). Maximum temperature trends tend towards warming that is stronger over the Great Lakes, the interior western and the northeastern contiguous United States. A warming hole in the Midwest generally decreases in size and magnitude when heat stress trends are calculated because the region has increasing moisture. CRU and nearly all reanalyses find cooling in the northern high plains that is not found in NOAA Climate Division trends. These NOAA trends are captured better by CRUTS401. Moistening in the northeast amplifies the heat stress there. Elsewhere the moisture trends are less clear. Drying over northern Texas (after 1996) in CRUTS401 translates into decreasing heat stress there (less so in CRUTS325). Though other reanalyses are not intended for long-term trends, MERRA-2 and ERA-Interim match observed trends better than other reanalyses.