The increasing cost of fossil-based energy sources has driven research in bio-based alternatives, such as perennial grasses for feedstock. The mid-Atlantic receives appreciable summer rainfall that may support a two-cut-per-year−1 harvest. At Virginia State University, a study on annual forage sorghum and two one-year stand perennials, miscanthus, and selected switchgrass ecotypes was carried out. The experimental design was a split-plot with harvest systems and feedstock grass species randomly assigned to the main and sub-plots, respectively. Only perennial grasses were assigned to the two-cut-per-year−1 system. The first cut occurred in early summer, and the second and single cut occurred after the frost-kill. Under the two-cut system, in 2022, the first-cut dry matter (DM) yield ranged from 8.9 Mg ha−1 in Blackwell to 14.7 Mg ha−1 in BoMaster. Additionally, except for BoMaster, the regrowth DM yields were within 10% of the first-cut DM yield. Under the one-cut system, the yield ranged from 10.8 Mg ha−1 in Blackwell to 23.2 Mg ha−1 in sorghum. Under the two-cut system, in 2023, miscanthus produced the greatest first-cut DM yield of 18.4 Mg ha−1, while other perennials averaged 10.1 Mg ha−1. Compared to the first cut, the hot and dry summer significantly reduced regrowth for all feedstock species, with the miscanthus DM yield dropping by 64%. While forage attributes differ among feedstock species, in general, both the first cut and regrowth showed greater crude protein and mineral elements, as well as lower ADF contents compared to a single cut following a killing freeze. Sorghum had better forage quality for the one-cut-per-year−1 feedstock material, and, along with the first cut and regrowth, it may have the potential for use as forage for maintenance energy in animal systems. For perennials, the two-cut-per-year−1 system removed the greatest quantities of nutrients during both years, with the first-cut harvest contributing about 65% of all removed N and K. Sorghum removed the greatest quantities of nutrients compared to the perennial under a one-cut-per-year−1 system. Therefore, while a two-cut-per-year−1 system can result in the greatest DM yields for dual-purpose use, its adoption calls for a critical analysis of economic benefits that considers feedstock bioenergy processing approaches, stand persistence, and fertilizer management strategies to address potential soil fertility depletion due to mineral element mining.