Chronic disease is becoming increasingly prevalent in Canada. Many of these diseases could be prevented by adoption of healthy lifestyle habits including physical activity and healthy eating. Men, especially those in rural areas, are disproportionately affected by chronic disease. However, men are often underrepresented in community-based chronic disease prevention and management (CDPM) programs, including those that focus on physical activity and/or healthy eating. The purpose of this study was to explore the experiences and perceptions of program delivery staff regarding the challenges in recruitment and participation of men in physical activity and healthy eating programs in rural communities, and suggestions for improvement. Semistructured interviews were conducted by telephone with 10 CDPM program delivery staff from rural communities in Southwest Ontario, Canada. Time and travel constraints, relying on spouses, and lack of male program leaders were cited as barriers that contributed to low participation levels by men in CDPM programs. Hiring qualified male instructors and engaging spouses were offered as strategies to increase men’s participation. The results of this study highlight many of the current issues faced by rural health organizations when offering CDPM programming to men. Health care organizations and program delivery staff can use the recommendations in this report to improve male participation levels.