Despite health benefits gained from physical activity and sport participation, older adults are less likely to be active. This study investigates what influences 50- to 75-year-olds (N = 439) to initiate and maintain walking football, across gender, socioeconomic status, number of health conditions, and physical activity level. It also considers relationships between participant characteristics and influences, and intentions to play after a forced break (COVID-19). Results of a U.K. online cross-sectional survey found those with two or more health conditions rated social influences significantly higher in initiation and maintenance than participants with no health conditions. Multiple regression analysis found a positive walking football culture, and perceived use of maintenance resources contributed significantly to intentions to return to play after COVID-19 restrictions eased. Practitioners should consider providing opportunities for social connection, foster a positive walking football culture, and encourage players to utilize maintenance resources (e.g., scheduling sessions) in older adult walking football sessions.