We combine observational data from Herald Canyon with high-resolution numerical model results from the Regional Arctic System Model (RASM) to assess the circulation and water mass characteristics in the Chukchi Sea. We find that a substantial fraction of water from the Chukchi Sea enters the East Siberian Sea south of Wrangel Island and circulates in an anticyclonic direction around the island. This water then contributes to the high-nutrient waters of Herald Canyon. Data were collected during the late summer over 3-day periods in 2008 and 2014 and show general similarities between the years, however there are differences in volume transport, temperature–salinity, and nutrient characteristics. To assess these differences, and also to get a wider temporal and spatial view, numerical modeling results from RASM are applied. In both observations and model results, Winter Water in 2014 was significantly fresher than in 2008. This freshening is concurrent with the large-scale freshening of the Arctic Ocean over recent decades, particularly in the Canada Basin. According to model results, high-frequency variability dominates the flow in Herald Canyon, which leads us to conclude that this region needs to be monitored over a longer time frame to deduce the temporal variability and potential trends. This investigation shows the highly dynamic conditions in the western Chukchi Sea and pinpoints a need for long-term monitoring of transport and biochemical properties in Herald Canyon to better understand its role in supply to the central Arctic Ocean.