Heat stress with measurable effects in dairy cattle is a growing concern in temperate regions. Heat stress in temperate regions differs between environments with different geophysical characteristics. Microclimates specific to each environment were found to greatly impact at what level heat stress occurs and will occur in the future. The landlocked state of Baden-Württemberg, Germany, provides several different environments, hence, a good case-study. Temperature-Humidity Index (THI) from 17 weather stations for the years 2003 to 2022 was calculated and milking yields from 22 farms for the years 2017 to 2022 were collected. The occurrences and evolving patterns of heat stress were analyzed with the use of a THI, and the effect of heat stress on milk yield was analyzed based on milking records from Automated Milking Systems. Daily average THI was calculated using hourly readings of relative humidity and ambient temperature, disregarding solar radiation and wind, as all animals were permanently stabled. Based on studies conducted in Baden-Württemberg and neighboring regions, cited ahead in the section of THI, THI = 60 was the threshold for heat stress occurrence. Findings show that the heat stress period varied between stations from 64 to 120 d with THI ≥ 60 in a year. This aligns with yearly and summer averages, also steadily increasing from May to September. The length of the heat stress period was found to increase 1 extra day every year. Extreme weather events such as heat waves did not increase the heat stress period of that year in length but increased the average THI. Milk yield was found to be significantly (α = 0.05) different between counties grouped into different zones according to heat stress severity and rate of increase in daily average THI. Future attempts at managing heat stress on dairy cattle farms in the temperate regions should account for microclimate, as geographical proximity does not mean that the increase in heat stress severity will be the same in the 2 neighboring areas.