In this master thesis, I explore how the field of Interaction Design might contribute in creating new platforms for engagement and expression, by involving a participatory culture of skateboarders in a Do It Yourself (DIY) project. The objective of the project was to give skaters an opportunity to experience the maker culture by sketching with technology, sharing their ideas within creative making, and participate in envisioning co-created skating spaces. Thus, the involvement and commitment of the participants were fundamental for this thesis. In total, twenty-eight members of the skateboarding community in Oslo were actively involved in the process of designing and making. The design process resulted in creating a physical prototype – an interactive skateboarding obstacle, using a DIY approach. It was based on the significance of DIY movement in the skateboarding culture uncovered by relevant literature, remarks of the participants and my own experience. My aim was to investigate what motivates and what hinders skateboarders from active engagement in shaping such spaces in Oslo. The methodology I chose was Research through Design (RtD). I found this methodology highly relevant since my wish was to see how a design process unfolds, and gives the participants a freedom to interpret and express the idea of combining skateboarding and interactivity. The process of designing and constructing the prototype become the sources of new knowledge. Together with the event that followed the making process, they helped me to determine the possibilities for the emergence of DIY culture involved in shaping “activist” spaces in urban environments.