A wheel pack assembly includes a pack portion wearable by a user and a wheeled portion removably coupled to the pack portion. The pack portion includes a support frame coupled to a rear surface thereof. The support frame includes articulating arms and stabilizing elements. The wheel portion includes a frame and a first wheel set coupled to the frame and disposed at a location spaced apart from a rear end of the wheeled portion. The frame includes a first portion and a second portion that are joined together at a bend and such that the second portion defines a transport bed of the assembly.