We analyzed online survey data from a longitudinal observational study on self-initiated ceremonial psychedelic use in older adults. Older adults attending psychedelic ceremonies showed higher levels of well-being at baseline when compared to matched younger adults. As in their younger counterparts, older adults report consistent acute subjective drug effects and improvements in mental health following the psychedelic ceremony, although changes were not as prominent as in younger adults. The presence of an underlying mental health disorder significantly predicted older adults’ well-being improvements following the psychedelic ceremony, while the level of challenging experiences during the psychedelic session predicted worsening mental health. Among healthy older adults, but not older adults suffering from a mental health disorder, interpersonal relational experiences during the acute psychedelic session predicted longitudinal well-being increases. Overall, these findings suggest that self-initiated psychedelic group sessions could potentially have beneficial effects on mental health of older adults.