The effect of pore morphology on capillary condensation and evaporation in nanoporous silicon is studied experimentally. A variety of cooperative and local effects are observed in tailored nanopores with well-defined regions by directly probing gas adsorption in each region using optical interferometry. All observations are ascribed to the ability of the nanopore region to access the gas reservoir directly and the nucleation of liquid bridges at local heterogeneities within the nanopore region. These assumptions, consistent with recent simulations, can be extended to any real nanoporous system.