This study examines the stages of change in exercise as a form of coping with chronic illness, among a panel of older adults managing arthritis, cardiovascular disease, or hypertension. Hypotheses connected to socio-demographic, exercise-history, cognitive, and illness contexts are explored in order to advance applications of the Transtheoretical Model for exercise self-care. A random sample of 735 individuals aged 51 to 95, who completed interviews at time 1 (1995–96) and time 2 (1996–97), were drawn from the Vancouver North Shore Self Care Study. Bivariate and hierarchical logistic regression analyses were performed on the data. The descriptive analyses supported two patterns: first, older persons with a chronic illness exhibited a propensity either to remain in or move into the extreme exercise stages (pre-contemplation or maintenance) in a non-sequential manner; second, elements of the illness context were primary determinants of stage of exercise change. Illness type, illness duration, activity restriction, and co-morbidity exhibited associations with exercise-stage change in the multivariate analysis. The findings have a number of direct implications for tailoring health promotion programs targetting older adults, especially those who use exercise as a form of self-care.