Winter annual legume cover crops often fail to reach full maturity by spring vegetable planting dates in northern climates, which prevents maximum nitrogen (N) contributions. To determine if delayed termination improved cover crop biomass and N content, we evaluated winter rye + hairy vetch (Secale cereale L. + Vicia villosa Roth) and oat + field pea (Avena sativa L. + Pisum sativum L.) cover crop mixtures in 2015 and 2016, and medium red clover (Trifolium pratense L.) in 2016, in zone-tilled organic yellow crookneck squash (Cucurbita pepo var. torticollis Harz). In-row regions where cover crops were terminated in early spring during crop row preparation were compared to between-row regions where termination was delayed until legume maturation in late spring. Soil quality (soil inorganic N, permanganate oxidizable C (POXC), and potentially mineralizable N (PMN)) was also determined for in-row and between-row regions at four time points throughout the growing season. In 2015, winter rye + hairy vetch biomass N more than doubled between early and late termination times, with 120 and 258 kg N ha−1, respectively. Permanganate oxidizable C was not responsive to cover crop systems or tillage, and only slightly decreased over time in 2016. Soil inorganic N and PMN after cover crop termination in 2016 provided evidence of localized soil N cycling responses to cover crop termination in in-row and between-row regions. The extended growing period for cover crops between crop rows in the first several weeks of crop growth had no negative effect on crop yield, and appeared to enhance soil fertility.