The food-retailing sector globally is undergoing tremendous change. In the Caribbean the changes appear to be unnoticed by academics, policy makers and development agencies. Supermarkets possibly are gaining market share at the expense of the traditional outlets utilized by small farmers. The organizational and institutional changes offer both opportunities and challenges for small farmers, the group that contributes the largest share of agricultural production in the Caribbean Region. Access to supermarket procurement systems, given their stringent quality and quantity requirements, is seen as the major challenge confronting small farmers. Ensuring them access to supermarket procurement systems is necessary if supermarkets are increasing in importance in Caribbean agri-food markets. This paper attempts to evaluate the importance of supermarkets in the Caribbean using data from Trinidad and Tobago and highlight some of the challenges that might confront small farmers during this period of tremendous change.