Abstract Background Older recently widowed women are faced with increased health risks and chronic conditions associated not only with bereavement, but also, older age. Loss and grief, adjusting to living alone, decreased income, and managing multiple chronic conditions can impact on older women’s ability to transition following recent spousal bereavement. Providing appropriate, timely, and effective services to foster this life transition is of critical importance, yet few services directed towards these women exist in Australia, and there is little data describing the experiences of women and their support needs at this time. Methods We conducted a longitudinal mixed method study using in-depth semi-structured interviews and questionnaires that were administered three times over a twelve month period to understand the experiences and needs of older women in the period following their husbands’ deaths. Descriptive statistics and Interpretive Phenomenological Analysis were used to analyse quantitative and qualitative data, respectively, prior to data integration. Results Participants were twenty-one community-dwelling recently widowed older women who were an average age of 71 (SD 6.13) years. The majority of participants scored within normal ranges of depression, anxiety, and stress, yet a subset of participants had elevated levels of each of these constructs (37%, 27%, and 19%, respectively) throughout the study period. Positive self-reports of general health predominated, yet 86% of participants were living with one or more chronic condition and taking an average of 4 medications per day. The majority (76%) experienced exacerbations of existing conditions or were diagnosed with a new illness in the early bereavement period, leading to planned and unplanned hospitalisations and other health service use. Qualitative data provided insight into these experiences, the meanings women ascribed to them, and their reasons for enacting certain health risk behaviours. Conclusions The combination of co-morbidities, polypharmacy, and risk behaviors impacted on medication management and appeared associated with health events. The feminization of ageing and an increasing number of older women living alone with multiple chronic conditions represent significant challenges to health services and societal support systems. Older women’s transition to widowhood signals concomitant health transitions and multidimensional support needs.