Evening Grosbeak (Coccothraustes vespertinus) populations have been hypothesized to be in steep decline across North America. Data characterizing long-term changes are needed to quantify the magnitude of the declines. We surveyed grosbeaks at a spring migratory stop-over site in Corvallis, Oregon, USA, where birds gather annually during April and May to feast on elm (Ulmus spp.) seeds before departing to breeding sites. An estimate produced by a statistics professor in the 1970s indicated peak numbers were 150,000 to 250,000 birds. Our surveys in 2013–2015 found annually variable numbers, from a few hundred grosbeaks in the lowest year to less than five thousand birds in the highest year. If the original estimate is approximately true, Evening Grosbeak numbers have experienced dramatic declines, averaging −2.6%/year, over the last four decades. Our local observation of declines during spring aligns with declines documented in winter across North America by bird feeder studies and in summer by the Breeding Bird Survey. We explore potential explanations for the changes in population size, such as influences of spruce budworm outbreaks, disease, and decreased structural diversity of forests owing to harvest practices. We also consider the challenges of interpreting changes in abundance of species with exceptionally variable populations, especially if population fluctuations or cycles may have long periodicities. Finally, we call for additional planned surveys to track the numbers of this enigmatic and charismatic species.