A field study was conducted to evaluate the influence of a trellis system, Genova double curtain (GDC), Scott Henry (SH), mid-wire that was vertical shoot positioned (VSP), and high wire cordon (HW), on fruit ripening and indirectly its influence on cold hardiness for cold-hardy, red wine grape cultivars, Marquette and Petite Pearl. In 2017, ‘Petite Pearl’ reached higher yields than ‘Marquette’, while VSP and SH trellis systems resulted in higher yields. However, in 2018, ‘Marquette’ had a greater yield than ‘Petite Pearl’. In 2019, 77.34% of ‘Marquette’ and 52.34% of ‘Petite Pearl’ had severe winter injury regardless of the trellis system. Unpredictable climate patterns in terms of growing degree-days, minimum winter air temperature, and rainfall manipulated both cultivars’ phenology during early establishment. Results suggest that under North Dakota climatic conditions, proper cultivar selection is more important than trellis system selection for sustainable grape production.