This study investigated the spatial distributions and long-term trends of the annual highest and lowest temperatures (summer peak temperature, SPT; winter peak temperature, WPT) and their timings (summer peak day, SPD; winter peak day, WPD) in South Korea and analyzed their relationship with the general circulation patterns. The two peaks were determined by selecting the highest and the lowest points after extracting temperature variations longer than the seasonal scale (91 days) in the time series of daily mean temperatures. For the long-term trend, we examined data for 100 years (1909–2008) for five stations and data for 35 years (1974–2008) for 61 stations. The SPD in South Korea is August 4 on average. It is earliest (July 31) in the central inland region, the central hilly sections, and the southern inland region and latest (August 10) in the southern coastal region and on Jeju Island (Seogwipo). The WPD in South Korea is January 16 on average. It is earliest (January 13) in the central inland region and southern inland region and latest (January 24) on Jeju Island (Jeju) and in Ulleungdo. The SPT and WPT are highest on Jeju Island (Seogwipo; 27.3 and 6.4 °C, respectively) and lowest in the central hilly sections (Daegwallyeong; 20.2 and −7.9 °C, respectively). The interannual variations in the WPD and WPT are greater than those in SPD and SPT. A significant increasing trend in the WPT was observed for all of the analyzed stations only for the second half of the 100-year period (1959–2008). In the case of the 35-year period, the SPD did not show any clear changes at all stations, but the WPD tended to occur earlier at three stations in the east coastal area. The WPT showed an increasing trend at 55 stations for 35 years, but the SPT showed an increasing trend only in Seogwipo (0.041 °C/year) and even showed a decreasing trend in Mungyeong (−0.049 °C/year). General circulation patterns were indexed and their correlations with the seasonal peaks were investigated. No correlations were found with the SPD. However, the WPD showed a significant positive correlation with the day of the highest Siberian High Intensity (SHI) and the day of the lowest Arctic Oscillation Index (AOI). Furthermore, the SPT showed negative correlations with the intensities of the Okhotsk High and North Pacific High, whereas the WPT showed a negative correlation with SHI and a positive correlation with AOI and with the intensity of the northerly wind that flows into the Korean Peninsula.