This study investigates the reasons for apparent differences in entrepreneurship rates in rural and urban areas using a Survey of Rural Kentucky Residents (SRKR) and the Panel Study of Entrepreneurial Dynamics (PSED) data. We estimate the determinants of dissimilar characteristics for rural and urban areas in two aspects: one is individual and contextual resources; the other is cultural tendencies of resources. The results of the analysis suggest that the difference in available individual, economic, and social support resources does not explain the observed difference in entrepreneurship rate. The results also indicate that gender, ethnicity, income, and number of children in the family have different effects on entrepreneurial intentions in rural and urban settings. The results suggest that policy makers need to account for cultural or geographical differences when designing entrepreneurial educational and support programs in order to enhance the establishment of new business between rural and urban areas.