This study compares high-resolution output (1.1-km horizontal grid length) from twice-daily forecasts produced by the Antarctic Mesoscale Prediction System (AMPS) with a dense observational network east of Ross Island. Covering 10 000 km2, 15 SNOWWEB stations significantly increased the number of observation stations in the area to 19 during the 2014–15 austral summer. Collocated “virtual stations” created from AMPS output are combined with observations, producing a single dataset of zonal and meridional wind components used to train a self-organizing map (SOM). The resulting SOM is used to individually classify the observational and AMPS datasets, producing a time series of classifications for each dataset directly comparable to the other. Analysis of class composites shows two dominant weather patterns: low but directionally variable winds and high but directionally constant winds linked to the Ross Ice Shelf airstream (RAS). During RAS events the AMPS and SNOWWEB data displayed good temporal class alignment with good surface wind correlation. SOM analysis shows that AMPS did not accurately forecast surface-level wind speed or direction during light wind conditions where synoptic forcing was weak; however, it was able to forecast the low wind period occurrence accurately. Coggins’s regimes provide synoptic-scale context and show a reduced synoptic pressure gradient during these classes, increasing reliance on the ability of Polar WRF to resolve mesoscale dynamics. Available initialization data have insufficient resolution for the region’s complex topography, which likely impacts performance. The SOM analysis methods used are shown to be effective for model validation and are widely applicable.