Objectives. Mental health professionals have suggested that widowed persons experience heightened psychological distress on dates that had special meaning for them and their late spouse, such as a wedding anniversary or the late spouse's birthday. This study examined the effects of such occasions on grief, anxiety, and depressive symptoms in a community sample of older widowed persons. Methods. OLS regression models were estimated using data from the Changing Lives of Older Couples (CLOC) study, a large prospective probability study of late-life widowhood. Participants were interviewed prior to and both 6 and 18 months after spousal loss; married matched controls were interviewed at comparable times. Results. Widowed persons reported heightened psychological distress when interviewed during the month of their late spouse's birthday, a post-holiday period (January), and in June, a month associated with wedding anniversaries and graduations in the United States. The distressing effects of special occasions on psychological symptoms were evidenced only within the first 6 months postloss, and were not apparent at the 18-month follow-up. Discussion. Our results support the clinical observation that persons in the early stages of spousal bereavement are at increased risk of psychological distress at times with special significance to the couple. We highlight methodological and clinical implications.