Cover crops are planted to reduce soil erosion, increase soil fertility, and improve watershed management. In the Delmarva Peninsula of the eastern United States, winter cover crops are essential for reducing nutrient and sediment losses from farmland. Cost-share programs have been created to incentivize cover crops to achieve conservation objectives. This program required that cover crops be planted and terminated within a specified time window. Usually, farmers report cover crop termination dates for each enrolled field (∼28,000 per year), and conservation district staff confirm the report with field visits within two weeks of termination. This verification process is labor-intensive and time-consuming and became restricted in 2020–2021 due to the COVID-19 pandemic. This study used Harmonized Landsat and Sentinel-2 (HLS, version 2.0) time-series data and the within-season termination (WIST) algorithm to detect cover crop termination dates over Maryland and the Delmarva Peninsula. The estimated remote sensing termination dates were compared to roadside surveys and to farmer-reported termination dates from the Maryland Department of Agriculture database for the 2020–2021 cover crop season. The results show that the WIST algorithm using HLS detected 94% of terminations (statuses) for the enrolled fields (n = 28,190). Among the detected terminations, about 49%, 72%, 84%, and 90% of remote sensing detected termination dates were within one, two, three, and four weeks of agreement to farmer-reported dates, respectively. A real-time simulation showed that the termination dates could be detected one week after termination operation using routinely available HLS data, and termination dates detected after mid-May are more reliable than those from early spring when the Normalized Difference Vegetation Index (NDVI) was low. We conclude that HLS imagery and the WIST algorithm provide a fast and consistent approach for generating near-real-time cover crop termination maps over large areas, which can be used to support cost-share program verification.