There is widespread speculation that baby boomers will make significant changes to the retirement landscape. Some attribute these changes, at least in part, to countercultural movements this generation pioneered during the sixties and seventies. However, empirical investigation into the long-term impact of countercultural identification in youth is scarce. To address this, our study examines associations between baby boomers’ retirement views and identification with counterculture. Using data from 6024 pre-retired Dutch older workers, we investigate whether greater identification with counterculture is associated with more active retirement views. Our results show that greater identification with counterculture is associated with more active retirement views, even when controlling for potential confounders. Beyond highlighting the diversity of the baby boom generation, these findings support the idea that (counter)cultural identity in youth has an impact across the life course and may therefore have implications for other key questions of life’s third age beyond retirement.