Two stages of the survey were conducted with more than 10,000 farm operators in the New England region to gather information of farm profiles, categories of multifunctional operations, farm operators’ demographics, farm labor situations, family decisions and support, entrepreneurial characteristics associated with farm enterprises and farm operators, challenges, barriers, and future outlook. Data analysis was completed using multivariate cluster analysis, geographic information system (GIS) mapping, and multivariate analysis of variances. Results indicated that small family farms were more entrepreneurial in terms of operation and networking capacity compared to large commercial agricultural producers. Small family farm operators also presented high levels of entrepreneurial characteristics such as taking control, being creative, and making independent and effective decisions. Risks were not serious concerns for all farm operators who responded to the survey. Small family farms believed that engaging in multifunctional operations indeed provided alternative income sources beyond selling conventional food and fiber products, and most of the small family farm operators had significant income from off-farm jobs. It was also noted that small family farms contributed more significantly to rural economic and intellectual mobility when they became more involved in promoting and strengthening local food systems.