The thesis investigates the way we live and travel overland in rural Canada. It explores the typology of the camp combined with the mobility of a trailer as a source for surveying temporary, outdoor dwelling, and the activities this mode of building supports. Recorded throughout the thesis is the design and construction of my own off-grid overland trailer named the Chuck Box. The work was completed using various tools and techniques which has been documented and presented on YouTube. The study focuses on outdoor activities with an emphasis on self-resiliency, connection to nature, and light-touch-down architectures as a means to be respectful in the Canadian wilderness. The Chuck Box aims to bridge the valuable experiences of roughing it in the back country with some of the modern-day comforts people have grown accustomed to even when living outdoors.