In cultivated landscapes, grasslands are an important land use type for insect life. Grassland management practices can have a significant impact on insect ecology. For example, intense fertilization and frequent cutting can reduce the diversity and abundance of insects by destroying their habitat and food sources. Thus, the quality of grassland habitat for insect development depends on its management intensity. The intensification of grassland production is discussed as one factor contributing to the decline in insect biomass over recent decades. Characterizing grassland changes over time provides one piece to the larger puzzle of insect decline. We analyzed landscape-level trends in grassland biomass near Orbroich and Wahnbachtal in North Rhine-Westphalia, Germany, over a 25-year period. In both areas, pronounced insect biomass decline had been observed. More than 430 Landsat images were used. An image normalization process was developed and employed to ensure that observed changes over time were attributed to grassland changes and not systemic changes inherent within image time series. Distinct clusters of grassland parcels were identified based on intensity and temporal changes in biomass using Normalized Difference Vegetation Index (NDVI) as an indicator. Cluster separability was confirmed using the Transform Divergence method. The results showed clusters having periods of distinct trends in vegetation biomass, indicating changes in grassland agronomic and/or management practices over time (e.g., fertilization, increased silage production). Changes in management practices coincided with regional trends in cultivation as documented by official statistics. We demonstrated the feasibility of using 100+ images over multiple decades to perform a long-term remote sensing analysis examining grassland change. These temporally expansive and spatially detailed trends of grassland change can be included as factors in the multi-variate analysis of insect decline. The methodology can be applied to other geographic areas. Such improved insights can support informed landscape design and cultivation patterns in relation to insect ecology and the broader context of biodiversity enhancement.