Hitchhiking has a long history as a form of alternative tourism and has experienced significant transformations in recent years due to the overall digitalisation of travel and culture. Similarly to other forms of mobilities, it was disrupted by the COVID-19 pandemic and non-pharmaceutical interventions aiming to stop the disease. The paper first defines hitchhiking as a social phenomenon and outlines its history from global and Polish perspectives. Then, it discusses the current developments and possible futures of hitchhiking culture. It is based first on the outline of the location of hitchhiking in contemporary popular culture, particularly Internet culture, and second on in-depth interviews with five young yet experienced lifestyle hitchhikers, performed during strict pandemic restrictions. The interviews focus on three major topics: modern challenges in hitchhiking, ITC (information and communication technologies) use, and hitchhiking during the pandemic. The results indicate the evolution of hitchhiking as a social phenomenon, where the cultural heritage of alternative lifestyles intertwines with the increasing role of the Internet and mobile communication. In conclusion, we postulate further studies, including applying new methodological approaches and asking research questions regarding, e.g. the commodification of tourism, the importance of web reputation, and interactions between hitchhikers, residents and drivers.