This study investigates how community-driven, small-scale events contribute to the regeneration of lesser known destinations, offering a vital alternative to mass tourism. It addresses the debate on the sustainable impact of events on local development, revealing more complex forms of regeneration, beyond temporary economic benefits. Our approach involves qualitative insights derived from 12 diverse Greek events, purposively selected by type and location. Responding to the limited research on practitioners’ perspectives, particularly in regional contexts, the methodology includes semi-structured interviews with organizers, focusing on their experiences, goals, collaborations and challenges related to tourism development and sustainability. Thematic analysis identified key findings. From the lens of organizers, the results underscore the strategic contribution of these local initiatives to Destination Regeneration. Six core themes emerged: Activation of Local Spaces, Local Identity and Social Cohesion, Economic and Tourism Stimulation, Resource Limitations in Planning, Stakeholder Engagement and Legacy, and Continuity Challenges. Organizers emphasized how events revitalize destinations by enhancing visibility, improving overall attractiveness, fostering community cohesion, and providing economic boosts year-round. While stakeholder collaboration is important, resource limitations and the need for sustained follow-up are critical. These events, despite limitations, are powerful catalysts for economic revitalization, social cohesion, and place-making, with implications for regional development.