Paleoclimatic evidence is necessary to place the current warming and drying of the western Mediterranean basin in a long-term perspective of natural climate variability. Annually resolved and absolutely dated temperature proxies south of the European Alps that extend back into medieval times are, however, mainly limited to measurements of maximum latewood density (MXD) from high-elevation conifers. Here, the authors present the world’s best replicated MXD site chronology of 414 living and relict Pinus uncinata trees found >2200 m above mean sea level (MSL) in the Spanish central Pyrenees. This composite record correlates significantly ( p ≤ 0.01) with May–June and August–September mean temperatures over most of the Iberian Peninsula and northern Africa ( r = 0.72; 1950–2014). Spanning the period 1186–2014 of the Common Era (CE), the new reconstruction reveals overall warmer conditions around 1200 and 1400, and again after around 1850. The coldest reconstructed summer in 1258 (−4.4°C compared to 1961–90) followed the largest known volcanic eruption of the CE. The twentieth century is characterized by pronounced summer cooling in the 1970s, subsequently rising temperatures until 2003, and a slowdown of warming afterward. Little agreement is found with climate model simulations that consistently overestimate recent summer warming and underestimate preindustrial temperature changes. Interannual–multidecadal covariability with regional hydroclimate includes summer pluvials after large volcanic eruptions. This study demonstrates the relevance of updating MXD-based temperature reconstructions, not only back in time but also toward the present, and emphasizes the importance of comparing temperature and hydroclimatic proxies, as well as model simulations for understanding regional climate dynamics.