1. Drifting, without responsibilities and obligations. 2. Carefree times to come. Other Explanations for TrampContinue ExploringTramp Spiritually, although this image initially appears to be negative, if we are prepared to work with it, it can have…Tramp The tramp personifies in us the wanderer, the freedom lover.In dreams he will often appear at a time when we…Tramp To dream of a tramp in the sense of a decrepit old wanderer links us back to the part of…Tramp (See Destitute; Hobo)Tramp One with like character; unstable, without rootsTramp A dream about a tramp denotes a fear of failure.