An external wheeled heeling apparatus for walking and running and transitioning to rolling on a surface is provided. The apparatus includes a sole having a forefoot, an arch and a heel portion provided with a first side of the heel portion and a second side of the heel portion. The forefoot operable to engage the surface for walking and running. The apparatus further includes a first wheel operably coupled to rotate adjacent the first side of the heel portion and a second wheel operably coupled to rotate adjacent the second side of the heel portion.