A network of 32 drought sensitive tree-ring chronologies is used to reconstruct mean water year flow on the Columbia River at The Dalles, Oregon, since 1750. The reconstruction explains 30 percent of the variability in mean water year (October to September) flow, with a large portion of unexplained variance caused by underestimates of the most severe low flow events. Residual statistics from the tree-ring reconstruction, as well as an identically specified instrumental reconstruction, exhibit positive trends over time. This finding suggests that the relationship between drought and streamflow has changed over time, supporting results from hydrologic models, which suggest that changes in land cover over the 20th Century have had measurable impacts on runoff production. Low pass filtering the flow record suggests that persistent low flows during the 1840s were probably the most severe of the past 250 years, but that flows during the 1930s were nearly as extreme. The period from 1950 to 1987 is anomalous in the context of this record for having no notable multiyear drought events. A comparison of the flow reconstruction to paleorecords of the Pacific Decadal Oscillation (PDO) and El Nifio/Southern Oscillation (ENSO) support a strong 20th Century link between large scale circulation and streamflow, but suggests that this link is very weak prior to 1900.