We developed CropPlantHarvest, the first long-term dataset of annual corn and soybean planting and harvesting dates across the U.S. Midwest at 500 m resolution for 2001–2024. Planting dates are estimated using the remotely sensed crop modeling system CropSow. Harvesting dates are retrieved using the novel Normalized Harvest Phenology Index (NHPI) to capture spectral transitions from senescent crops to crop residues. CropPlantHarvest is available at https://doi.org/10.5281/zenodo.16967482.