ABSTRACT Soil health is central to sustainable agriculture and a key goal of regenerative and organic farming. However, monitoring changes in soil health remains challenging due to the lack of regionally relevant benchmarks and context‐specific indicators. This study assessed the impacts of long‐term and combined regenerative management practices on soil health across 87 California vineyards with diverse management histories, microclimates, and soils. Three key indicators, including aggregate stability, mineralizable carbon, and soil organic carbon, were used to develop region‐specific soil health scoring functions. These were adapted from Cornell's Comprehensive Assessment of Soil Health and the Soil Health Institute frameworks. Indicator values generally trended lower than existing benchmarks, emphasizing the need for crop‐ and region‐specific scoring systems. Results from mixed‐effects models and fuzzy‐set qualitative comparative analysis (fsQCA) indicate that long‐term cover cropping (≥ 10 years) was the most consistent driver of high soil health scores, especially when combined with other practices. Livestock integration improved soil organic carbon and mineralizable carbon scores in under 10 years, showing potential to accelerate soil health benefits. Our results highlight the importance of tailoring practices to local soil and climate conditions. Findings also support the development of more flexible, regionally informed soil health frameworks.