Weed control is a challenging aspect of pumpkin production. Winter rye mulches may offer growers a means to manage weeds in pumpkin; however, rye degradation leads to an immobilization of soil nitrogen. Combining winter rye with a nitrogen fixing legume such as hairy vetch is an interesting option that may solve this problem. Twelve combinations including three hairy vetch seeding rates, two termination dates and the use or not of glyphosate before rolling cover crops were studied during the 2013 and 2014 growing seasons at the Laval University Agronomic Station in Saint-Augustin-de-Desmaures, Quebec, Canada to evaluate weed control and effects on pumpkin production. Adding hairy vetch to winter rye provided no benefits because of severe winterkill of the legume. Using glyphosate was necessary to prevent rye regrowth. Pumpkin growth was better and yields were higher than in the plots were no glyphosate was used. Mulches established at flowering (Zadoks 69) provided about 2,000 kg ha−1 more aboveground dry biomass than at early heading (Zadoks 51). This high biomass was essential in glyphosate treated plots in order to maintain excellent weed control throughout the growing season. When compared with the no-mulch weed-free control, yield in Zadoks 69+glyphosate treatment was lower in 2013 but comparable in 2014.