Three years of continuous Spray glider observations in the southern California Current System (CCS) are combined with a numerical simulation to describe the mean and variability of poleward flows in the southern CCS. Gliders provide upper ocean observations with good across‐shore and temporal resolution along two across‐shore survey lines while the numerical simulation provides a dynamically consistent estimate of the ocean state. Persistent poleward flows are observed in three areas: within 100 km of the coast at Point Conception, within the Southern California Bight (SCB), and offshore of the SCB and the Santa Rosa Ridge (SRR). Poleward transport by the flows within the SCB and offshore of the SRR exceeds the poleward transport off Point Conception, suggesting that the poleward flows are not continuous over the 225 km between observation lines. The numerical simulation shows offshore transport between the survey lines that is consistent with some of the poleward flow turning offshore before reaching Point Conception. The poleward current offshore of the SRR is unique in that it is strongest at depths greater than 350 m and it is observed to migrate westward away from the coast. This westward propagation is tied to westward propagating density anomalies originating in the SCB during the spring‐summer upwelling season when wind stress curl is most strongly positive. The across‐shore wave number, frequency, and phase speed of the westward propagation and the lack of across‐shore transport of salinity along isopycnals are consistent with first‐mode baroclinic Rossby dynamics.