A caster assembly for use with varies structures, including ladders and elevated platforms is provided. In one embodiment, the caster assembly includes a first wheel coupled with a first bracket and configured to rotate about a first axis relative to the first bracket. A shaft is coupled to the first bracket as well as to a second bracket. The first bracket is rotatable relative to the second bracket about a second axis, which may be coincident with, or parallel to, an axis of the shaft. A third bracket is coupled with the shaft and is rotatable about the second axis, the third bracket being selectively locked in at least two positions relative to the second bracket. A second wheel is coupled with the third bracket, the second wheel being rotatable relative to the third bracket about a third axis.