As global warming gets worse, the extreme heat exposure time is expected to increase. Considering that the heatwave damages increased by the accumulation of heat stress, it is important to understand the heatwave onset and number of heatwave days (HWDs). Here, we show that the end of East Asian summer monsoon activity (i.e., Changma retreat date, CRD) could be an indicator in determining the onset of the heatwave, and the barotropic structure induced by the circumglobal and Pacific–Japan teleconnections is a key factor in lengthening the number of HWDs in Korea. The onset of the heatwave is delayed when CRD belated than the climatology late over Korea due to sufficient moisture transportation between the edge of western North Pacific subtropical high and cold polar air mass in July. The number of HWDs from July through August over Korea shows a positive linear relationship with the synoptic stagnation index because the upper-layer anticyclone associated with stagnation is formed around Korea by zonal wave activity. Barotropic anticyclone stabilizes the atmosphere and increases the number of clear sky days, which possibly leads to hot days. Fewer HWDs are observed when there is baroclinic instability due to strong upper-level jet stream and synoptic-scale weather systems move smoothly. By identifying the meteorological mechanism of heatwave occurrence and favorable conditions for sustained hot days over Korea, our results are eventually able to contribute to reducing damages caused by heatwaves.