Lately, the Hill Pond Rice System (HPRS) is being promoted as a form of alternative farming systems in selected northern provinces of Thailand, in which the land conversion is designed to maximize rainwater harvesting in farmland consisting of forest trees, water reservoirs, paddy fields, and high-value crop cultivation to serve environmental and livelihood needs. This study employed the double-hurdle model and the tobit technique to investigate the farm-level factors associated with land conversion from maize monocropping to the HPRS using primary data collected from 253 households in Nan, Chiang Mai, Tak, and Lampang Provinces. It was found that education, farming knowledge, understanding benefits of the HPRS, access to water sources, access to advis, and workforce sharing raised the likelihood and extent of farmland conversion into the HPRS. In contrast, perceived complexity of the HPRS, experiences with negative shocks, and land tenure security lowered the likelihood and extent of land conversion. The findings suggest that on-farm collective action should be promoted to mitigate labor constraints in implementation and that access to equipment should be enhanced through HPRS advisors’ visits.