Introduction: Physical activity (PA), particularly low-impact activities like bicycling, can improve health in older adults. However, bicycling rates are lower in the Midwest than other regions in the United States. Therefore, it is important to identify unique social, personal, and environmental factors that inhibit or promote bicycling, and how these are associated with PA. The influences of these factors were explored using the social ecological model. Method: A cross-sectional online survey was developed using previously validated local and national bicycling questionnaires, then distributed to Midwestern bicyclists 50 years and older. Exploratory factor analysis was conducted to understand the influences of social, personal, and environmental barriers and promoters on bicycling patterns. All models were conducted separately by gender, and accounted for age, race, education, marital status, income, and employment. Results: Social promoters (B = 0.386, p = 0.002), such as having friends/family that bicycle were associated with greater PA. Personal promoters (B = -0.311, p = 0.006) such as needing to lose weight were associated with reduced PA. Environmental factors had no associations with PA. However, individual environmental components, such as number of vehicles on the roads, were significantly associated with PA for both males and females. Females reported more barriers than males. The overall model accounted for 16.1% of the total variance in PA levels. Conclusion: Interventions to promote PA via bicycling in older adults should focus on social factors, while also reducing personal-level factors for males. Interventions for females could focus on reducing specific personal, social, and environmental barriers.