The paucity of available instrumental climate records in cold and arid regions of the western Himalaya, India, hampers our understanding of the long-term variability of regional droughts, which seriously affect the agrarian economy of the region. Using ring width chronologies of Cedrus deodara and Pinus gerardiana together from a network of moisture-stressed sites, Palmer Drought Severity Index values for October–May back to 1310 A.D. were developed. The twentieth century features dominant decadal-scale pluvial phases (1981–1995, 1952–1968, and 1918–1934) as compared to the severe droughts in the early seventeenth century (1617–1640) as well as late fifteenth to early sixteenth (1491–1526) centuries. The drought anomalies are positively (negatively) associated with central Pacific (Indo-Pacific Warm Pool) sea surface temperature anomalies. However, non-stationarity in such relationships appears to be the major riddle in the predictability of long-term droughts much needed for the sustainable development of the ecologically sensitive region of the Himalayas.