Small-scale dairy farming is economically challenging; however, management intensive grazing practices have allowed many farms to become profitable. Traditional barn housing during cold seasons is a large expense and could be adapted to further economic gains. In this study, three cold season pasture management practices, such as bedded pack (BP) compost amendment, out-wintering (OW) on pasture, and stockpiling (SP) mixed grass–legume pasture forage, were evaluated for impact to soil and forage quality within pasture. Composite soil and forage samples were collected during spring and autumn 2009–2010 for soil physical, chemical, and biological analyses (nematode community structure) and forage quality. Out-wintering favored fungal decomposition (P = 0.089), and all treatments promoted soil food web structure, with a mean structure index value of 63 ± 1.71 SE. Negative impacts to soil health, including physical structure and soil chemistry, were not detected. Impacts to forage quality included decreased degradable protein under SP (P = 0.055) and decreasing relative feed value following SP and BP treatment application (P = 0.025). The small sample size (total n = 16 or eight pairs) and high variability require cautious interpretation, yet minimal negative effects of implementing BP, OW, and SP practices were detected.