Abstract Experimental observations from coastal and island wind profilers, aircraft, and other sensors deployed during the California Land-falling Jets Experiment of 1997/98 and the Pacific Land-falling Jets Experiment of 2000/01–2003/04 were combined with observations from operational networks to document the regular occurrence and characteristic structure of shallow (∼400–500 m deep), cold airstreams flowing westward through California’s Petaluma Gap from the Central Valley to the coast during the winter months. The Petaluma Gap, which is the only major air shed outlet from the Central Valley, is ∼35–50 km wide and has walls extending, at most, a modest 600–900 m above the valley floor. Based on this geometry, together with winter meteorological conditions typical of the region (e.g., cold air pooled in the Central Valley and approaching extratropical cyclones), this gap is predisposed to generating westward-directed ageostrophic flows driven by along-gap pressure differences. Two case studies and a five-winter composite analysis of 62 gap-flow cases are presented here to show that flows through the Petaluma Gap significantly impact local distributions of wind, temperature, precipitation, and atmospheric pollutants. These gap flows preferentially occur in pre-cold-frontal conditions, largely because sea level pressure decreases westward along the gap in a stably stratified atmosphere in advance of approaching cold-frontal pressure troughs. Airstreams exiting the Petaluma Gap are only several hundred meters deep and characterized by relatively cold, easterly flow capped by a layer of enhanced static stability and directional vertical wind shear. Airborne air-chemistry observations collected offshore by the NOAA P-3 aircraft illustrate the fact that gap-flow events can transport pollutants from inland to the coast, and that they can contribute to coastally blocked airstreams. The strongest gap-flow cases occur when comparatively deep midtropospheric troughs approach the coast, while the weak cases are tied to anticyclonic conditions aloft. Low-level cold-frontal pressure troughs approaching the coast are stronger and possess a greater along-gap pressure gradient for the strong gap-flow cases. These synoptic characteristics are dynamically consistent with coastal wind profiler observations of stronger low-level gap flow and winds aloft, and greater rainfall, during the strong gap-flow events. However, gap flow, on average, inhibits rainfall at the coast.