Conventional agriculture often aims to achieve high returns without allowing for sustainable natural resource management. To prevent environmental degradation, agricultural systems must be assessed and environmental standards need to be developed. This study used a multi-factor approach to assess the potential environmental impact risk of six diverse systems: five production systems and a successional system or abandoned agronomic field. Assessment factors were soil quality status, amount of pesticide and fertilizer applied and tillage intensity. The assessment identified the best management practices (BMP)–conventional tillage system as a high-risk system mostly because of extensive tillage. The certified organic system was also extensively tilled and was characterized by P build-up in the soil, but performed well based on other assessment factors. Conversely, the BMP–no tillage and the crop–animal integrated system were characterized as low risk mainly because of reduced tillage. The paper discusses assessment strengths and weaknesses, ways to improve indicators used, and the need for additional indicators. We concluded that with further development the technique will become a resourceful tool to promote agricultural sustainability and environmental stewardship and assist policy-making processes.