Our ability to improve prognostic modeling of the Greenland Ice Sheet relies on understanding the long-term relationships between climate and mass flux (via iceberg calving) from marine-terminating tidewater glaciers (TWGs). Observations of recent TWG behavior are widely available, but long-term records of TWG advance are currently lacking. We present glacial geomorphological, sedimentological, archaeological, and modeling data to reconstruct the similar to 20 km advance of Kangiata Nunaata Sermia (KNS; the largest tidewater glacier in southwest Greenland) during the first half of the past millennium. The data show that KNS advanced similar to 15 km during the 12th and 13th centuries CE at a rate of similar to 115 m a(-1), contemporaneous with regional climate cooling toward the Little Ice Age and comparable to rates of TWG retreat witnessed over the past similar to 200 years. Presence of Norse farmsteads proximal to KNS demonstrates their resilience to climate change, manifest as a rapidly advancing TWG in a cooling climate. The results place limits on the magnitude of ice-margin advance and demonstrate TWG sensitivity to climate cooling as well as warming. These data combined with our grounding-line stability analysis provide a long-term record that validates approaches to numerical modeling aiming to link calving to climate.