The Hawaiian Islands have been identified as a global biodiversity hotspot. We examine the Normalized Difference Vegetation Index (NDVI) using Climate Data Records products (0.05 × 0.05°) to identify significant differences in NDVI between neutral El Niño-Southern Oscillation years (1984, 2019) and significant long-term changes over the entire time series (1982–2019) for the Hawaiian Islands and six land cover classes. Overall, there has been a significant decline in NDVI (i.e., browning) across the Hawaiian Islands from 1982 to 2019 with the islands of Lāna’i and Hawai’i experiencing the greatest decreases in NDVI (≥44%). All land cover classes significantly decreased in NDVI for most months, especially during the wet season month of March. Native vegetation cover across all islands also experienced significant declines in NDVI, with the leeward, southwestern side of the island of Hawai’i experiencing the greatest declines. The long-term trends in the annual total precipitation and annual mean Palmer Drought Severity Index (PDSI) for 1982–2019 on the Hawaiian Islands show significant concurrent declines. Primarily positive correlations between the native ecosystem NDVI and precipitation imply that significant decreases in precipitation may exacerbate the decrease in NDVI of native ecosystems. NDVI-PDSI correlations were primarily negative on the windward side of the islands and positive on the leeward sides, suggesting a higher sensitivity to drought for leeward native ecosystems. Multi-decadal time series and spatially explicit data for native landscapes provide natural resource managers with long-term trends and monthly changes associated with vegetation health and stability.