The complex export pathways that connect the surface waters of the Weddell Sea with the Antarctic Circumpolar Current influence water mass modification, nutrient fluxes, and ecosystem dynamics. To study this exchange, 40 surface drifters, equipped with temperature sensors, were released into the northwestern Weddell Sea’s continental shelf and slope frontal system in late January 2012. Comparison of the drifter trajectories with a similar deployment in early February 2007 provides insight into the interannual variability of the surface circulation in this region. Observed differences in the 2007 and 2012 drifter trajectories are related to a variable surface circulation responding to changes in wind stress curl over the Weddell Gyre. Differences between northwestern Weddell Sea properties in 2007 and 2012 include 1) an enhanced cyclonic wind stress forcing over the Weddell Gyre in 2012; 2) an acceleration of the Antarctic Slope Current (ASC) and an offshore shift of the primary drifter export pathway in 2012; and 3) a strengthening of the Coastal Current (CC) over the continental shelf in 2007. The relationship between wind stress forcing and surface circulation is reproduced over a longer time period in virtual drifter deployments advected by a remotely sensed surface velocity product. The mean offshore position and speed of the drifter trajectories are correlated with the wind stress curl over the Weddell Gyre, although with different temporal lags. The drifter observations are consistent with recent modeling studies suggesting that Weddell Sea boundary current variability can significantly impact the rate and source of exported surface waters to the Scotia Sea, a process that determines regional chlorophyll distributions.