The potential market for locally produced organic cherry tomatoes (Solanum lycopersicum var. cerasiforme) is large in Canada, but it is challenging to grow this warm-season crop in open fields (OFs) due to the cool and short growing season. To test the feasibility of using high tunnels (HTs) for improving organic production in southern Ontario, plant growth, fruit yield and quality, and pest and disease incidence were compared for ‘Sarina hybrid’ cherry tomato among three production systems: OF, HT, and high tunnel with anti-insect netting (HTN) in Guelph, ON, in 2015 and 2016. Averaged over the 2 yr, the highest marketable fruit yield was achieved in HT (≈70 t ha^-1), followed by HTN (≈50 t ha^-1), with the lowest yield obtained in OF (≈24 t ha^-1). Compared with OF, increased plant growth, extended harvest period, reduced pest numbers, and increased proportion of marketable fruits all led to the higher marketable yields in HT and HTN. Under HT vs. OF, fruit quality attributes, such as soluble solids content and post-harvest water loss, were better in 2015 and similar in 2016. Although the insect netting reduced pest incidence and disease infection, fruits harvested from HTN had lower yield, smaller size, and lower soluble solids content than those from HT in both years. Therefore, HT can be recommended for organic production of cherry tomatoes in southern Ontario.