Employers are implementing workplace health promotion programs that address modifiable health risk factors such as overweight and obesity, smoking, high blood pressure, high cholesterol, physical inactivity, poor diet, and high stress. Research with large employers has found that these programs can improve workers’ health and decrease the costs associated with medical care, absenteeism, and presenteeism. Despite their promise, health promotion programs are not widely embraced by small businesses, especially those in rural communities. This article reviews the barriers encountered by small and rural businesses in implementing health promotion programs. We describe an approach developed in cooperation with the New York State Department of Health’s Healthy Heart Program and the Cayuga Community Health Network to engage small businesses in health promotion. We review the development and implementation of an assessment tool created to evaluate current workplace health promotion programs, policies, and practices targeting cardiovascular disease among small, rural employers in upstate New York. Potential benefits of the assessment tool are discussed, and the instrument is made available for the public.