High tunnels and greenhouses effectively extend the growing season and protect crops from adverse environmental conditions. However, production in the less expensive and portable caterpillar tunnel has not been reported. The research aimed to evaluate the phenology, yield and quality of eight paste tomato, eight bell pepper, and two cold-hardy wine grapes grown in the caterpillar tunnel compared to the open field. In 2022, tomato and bell pepper cultivars were severely affected by tomato spotted wilt virus. Caterpillar tunnels extended the growing season and accelerated the key phenological stages of all three species. The tunnel increased the yield and quality of tomato and bell pepper. Impacts on wine grape yield across production systems were inconsistent, however the caterpillar tunnel showed potential for improving grape quality. ‘Marquette’ showed greater winter hardiness in the tunnel, while ‘Petite Pearl’ showed reduced winter hardiness in the caterpillar tunnel compared to open field production system.