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While Kramers' rates have been studied for almost a century, the transition path time between states has only recently received attention. Transition paths between different energy levels are expected to be indistinguishable in shape and have equal uphill and downhill lengths. This fundamental symmetry often prevents directional sensing in experiments. Here, we report experimental evidence for transition path time symmetry and its breakdown on the single-molecule and mesoscale. In automated Brownian dynamics experiments, we establish first-passage time symmetries of colloids driven by femtoNewton-range forces in holographically-created optical landscapes confined in microchannels. Conversely, we show that transitions which couple in a path-dependent manner to fluctuating forces exhibit asymmetry. We reproduce this asymmetry in folding transitions of DNA-hairpins driven out of equilibrium and suggest a topological mechanism for the symmetry breakdown. Our results can reveal directionality in molecular transitions or translocations through membrane channels and nanopores.