A tracked vehicle, or a kit for converting a standard bicycle into a tracked cycle, includes a track assembly with a bogie assembly for riding on snow, mud, sand, etc. The track assembly includes a continuous track movably disposed about a drive wheel coupled to a frame of the vehicle or bike, and a bogie wheel disposed rearward of the drive wheel. The bogie assembly includes a pair of arms coupling the bogie wheel to the frame of the vehicle or bike in a cantilever fashion.