The hemlock woolly adelgid is a serious pest of Eastern and Carolina hemlock in the eastern United States. Successfully managing the hemlock resource in the region depends on careful monitoring of the spread of this invasive pest and the targeted application of management options such as biological control, chemical, or silvicultural treatments. To inform these management activities and test the applicability of a landscape-scale remote sensing effort to monitor hemlock condition, hyperspectral collections, and concurrent ground-truthing in 2001 and 2012 of hemlock condition were compared with field metrics spanning a 10-yr survey in the Catskills region of New York. Fine twig dieback significantly increased from 9 to 15% and live crown ratio significantly decreased from 67 to 56% in 2001 and 2012, respectively. We found a significant shift from 59% “healthy” hemlock in 2001 to only 16% in 2012. However, this shift from healthy to declining classifications was mostly a shift to decline class 2 “early decline”. These results indicate that while there has been significant increase in decline symptoms as measured in both field and remote sensing assessments, a majority of the declining areas identified in the resulting spatial coverages remain in the “early decline” category and widespread mortality has not yet occurred. While this slow decline across the region stands in contrast to many reports of mortality within 10 yr, the results from this work are in line with other long-term monitoring studies and indicate that armed with the spatial information provided here, continued management strategies can be focused on particular areas to help control the further decline of hemlock in the region.