We report measurements and numerical simulations of ultrafast laser-excited carrier flow across a scanning tunneling microscope (STM) junction. The current from a nanoscopic tungsten tip across a ∼1 nm vacuum gap to a silver surface is driven by a two-color excitation scheme that uses an optical delay-modulation technique to extract the two-color signal from background contributions. The role of optical field enhancements in driving the current is investigated using density functional theory and full three-dimensional finite-difference time-domain computations. We find that simulated field-enhanced two-photon photoemission (2PPE) currents are in excellent agreement with the observed exponential decay of the two-color photoexcited current with increasing tip-surface separation, as well as its optical-delay dependence. The results suggest an approach to 2PPE with simultaneous subpicosecond temporal and nanometer spatial resolution.