There is a myriad of motivations and barriers that influence agricultural producers to adopt ecologically-sound management practices. Therefore, this research aims to explore vintners' motivations to adopt organic, biodynamic, and sustainable practices in the Niagara region. This research also investigates what the challenges are in the transition process, and whether the regulations facilitate or hinder producers from completing the transition. This research employs a survey of regulations, semi-structured interviews, and online questionnaires to acquire data on vintners' experiences. The results conclude that Niagara's wineries are motivated to adopt ecologically-sound management practices due to environmental, social, and economic reasons. The results also indicate that there is a paradox of sustainability among organic, biodynamic, and sustainable producers on which practice is considered environmentally friendly. Lastly, the findings reveal that the wineries did not encounter severe challenges during transition, however, they note that the regulatory requirements and certification process need to improve.