Smallholder dairy farms encounter challenges in minimal production factors that result in a lack of family income. They react differently to these limits by combining on-farm and off-farm activities (diversifying activity), concentrating exclusively on milk production (specializing activity), or leaving the dairy production to secure family livelihood. As far as adaptive strategies are concerned, they may affect milk production growth at the farm and national levels. We performed an observational case study in the West Java Province (Indonesia) to resolve those problems. We gathered information in two phases: a systematic survey (May to September 2015) to 355 farms and an in-depth interview (January to April 2017) with 20 farms. Our result distinguishes four categories of farms, along with a very small specialized dairy farm (T1), a combination of the dairy farm off-farm activity with very limited land (T2), a small specialized dairy farm (T3), and a mixed crop-dairy farm (T4). The technical-economic value varies depending on the farm type. The six trajectories prevail. The main change was the addition of off-farm activities for poor farmers. Farms in the development trajectory, two strategies coexist between the dairy production system's specialization and the mixed crops-dairy system. In conclusion, this study underscored each farm trajectory's different attributes and drivers. The study also underlined the importance of the initial capital of smallholders to illustrate their future farm trajectory.