The rise of remote work and collaborative workspaces (CWS) offers new opportunities for rural areas to attract talent, foster community engagement, social revitalization, and economic resilience. This chapter explores the potential of rural CWSs, focusing on the impact of short-term coworking experiences in Portugal on social capital and regional development. Drawing on participant observation in two rural CWS initiatives, supported by interviews and focus groups with key stakeholders, the chapter highlights the challenges and opportunities faced by these spaces. It identifies key barriers, such as infrastructural limitations, cultural integration issues, and a lack of strategic alignment among local actors. At the same time, it demonstrates how short-term coworking experiences can strengthen social capital by fostering connections between coworkers, local communities, and regional institutions. The chapter offers practical recommendations for improving rural CWS strategies, emphasizing the importance of community-building, collaboration, co-creation, and effective communication, providing valuable resources for researchers, policymakers, and practitioners interested in leveraging these spaces for sustainable rural development.