Season extension structures like high tunnels make it possible to produce cold-tolerant crops during winter months for both a longer cropping season and a winter market season. The effects of location and planting date on the fresh yield of several cultivars of Asian greens (Brassica rapa L.), lettuce (Lactuca sativa L.), and spinach (Spinacia oleracea L.) were examined at Moscow, ID/Pullman, WA, and Vancouver, WA, a cold temperate climate and a mild marine climate, respectively. In Winter 2005–06, 20 cultivars were evaluated and in Winter 2006–07 a subset of 12 cultivars were evaluated. Location impacted yield, and higher yields overall were attained at Vancouver than at Moscow/Pullman, likely as a result of more consistent, warmer soil and air temperatures as well as increasing irradiance in February and March at Vancouver. Asian green cultivars had the highest overall yield resulting from faster growth compared with spinach and lettuce cultivars at both locations. Although most lettuce cultivars grew throughout the winter, further research is needed to identify the most suitable cultivars, seeding dates, and planting densities to optimize winter production of this crop and for Asian greens and spinach. Planting date influenced yields with the highest yields obtained for the third planting date for all trials except at Moscow/Pullman in the second year. Overall, this research suggests that it is possible to grow many cold-tolerant cultivars of Asian greens, spinach, and lettuce in a high tunnel during the winter months in both mild and cold temperate northern climates.