On a basic level, a skateboard is realistically just a simple toy. It consists of a wooden board made out of 7 plies of laminate wood glued together, two metal turning mechanisms known as trucks, wheels with bearings inside, nuts and bolts to hold it all together, and a sheet of griptape, which is more or less sandpaper with an adhesive backing stuck to the wooden deck. Fundamentally, this toy provides the user with the ability to travel from one location to another at a quicker pace; however, what lies beneath the surface is the ability to unlock different worlds and change the user’s impression of the built environment around them. Without a skateboarder interpreting the landscape, determining the appropriate trick for a specific location, and unlocking new feats otherwise deemed impossible, the skateboard stays a toy. Skateboarding is considered by most to be a sport, or a blending of self-expression, physical prowess, and artistic interpretation of the landscape. This work aims to provide an overview of skateboarding, including its origins and evolution over time, the history of skateparks, and its current state. It will build a case that skateboarding has been actively planned against and treated as a nuisance in the public realm, and because of this, negative perceptions have lingered for too long. It will focus on newly developed landscapes that provide skateboarding and pedestrians a shared location that dispelling misperceptions and providing a landscape that is more friendly for skateboarding. Finally, it will show how, through landscape architecture interventions, these spaces can be designed to integrate recreation into the urban fabric, creating opportunities for expression and creativity while not compromising the pedestrian experience, but rather providing opportunities to gather and spectate.