Due to the recent changes in the economy of Kentucky tobacco production, some producers are seeking an alternative crop that will provide similar economic gains to tobacco without needing more acreage. Tomatoes are an existing crop in Kentucky that have been declining in acreage over the last five years. There is evidence to suggest that, through niche and local marketing, tomatoes may be able to fill the void left by tobacco. However, there is concern among producers that they will lose yield and/or quality if they switch to one of these niche production systems or cultivars. A two year study at Western Kentucky University compared the yield and quality of three tomato cultivars, two heirlooms and one hybrid, under organic and conventional management techniques to see if producers concerns are valid. The heirloom cultivars used were 'Cherokee Purple' (CP) and 'Mr. Stripey', (MS) the hybrid cultivar was 'Crista' (CR). The study was a split block design, with four randomized replications within each block. Plants were grown under black plastic mulch, with drip irrigation under the mulch. Plants were harvested weekly throughout the season and data were collected on individual fruit weight, size, grade and the number of fruit produced per plant. Production and quality were compared between management techniques for each cultivar, and the cultivars were compared to each other under individual management techniques. When comparing organic and conventional management practices, CP produced significantly (p<.05) larger, heavier, and higher quality fruit under organic practices and showed no significant differences in fruit number in 2008. MS and CR showed no significant differences between production systems for fruit weight or size, CR produced significantly higher quality fruit under conventional treatment and MS produced significantly more fruit per plant in 2008. In 2009, CP did not produce enough fruit under organic management to allow statistical comparison between management systems. MS however did not show any significant differences between management systems for any of the traits studied. CR produced significantly larger fruit under organic management, but no other differences were observed. When comparing cultivars in 2008, CP and CR produced fruit of similar weight but significantly heavier than MS under both production systems. CP produced the largest fruit under organic management, with CR following and MS producing the smallest fruit. Under conventional management, CP and CR produced fruit of similar size and both were larger than MS. MS produced the highest quality fruit under organic management, and CR produced the nicest grade under conventional management. No differences were seen for number of fruit per plant between cultivars under organic management, while MS produced the most fruit per plant under conventional management. In 2009 CP did not produce enough fruit to be statistically compared to the other cultivars under organic management. MS and CR produced fruit of similar weight under both organic and conventional management, while CP produced the greatest weight under conventional management. CR produced larger fruit than MS under organic management, while under conventional management CP and CR were of similar size as were CR and MS, but CP was significantly larger than MS. No significant differences were found between cultivars for fruit grade or number of fruit per plant under either management system in 2009.