Little Ice Age (14th--19th centuries A.D.) glacial maxima and 20th century retreat have been well documented in Glacier National Park, Montana, USA. However, the influence of regional and Pacific Basin driven climate variability on these events is poorly understood. We use tree-ring reconstructions of North Pacific surface temperature anomalies and summer drought as proxies for winter glacial accumulation and summer ablation, respectively, over the past three centuries. These records show that the 1850's glacial maximum was likely produced by ~70 yrs of cool/wet summers coupled with high snowpack. Post 1850, glacial retreat coincides with an extended period (>50 yr) of summer drought and low snowpack culminating in the exceptional events of 1917 to 1941 when retreat rates for some glaciers exceeded 100 m/yr. This research highlights potential local and ocean-based drivers of glacial dynamics, and difficulties in separating the effects of global climate change from regional expressions of decadal-scale climate variability.