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Amenity migration in the Intermountain West is a rapidly evolving process that has greatly impacted wellbeing in many rural communities over the past several decades. While the impacts of amenity migration have been discussed through both individual community case studies and cross‐community comparative analysis, there is an ongoing need for research that continues to build upon our understanding of amenity migration's effects on individual and community wellbeing. Remote and hybrid work opportunities, expanded during the COVID‐19 pandemic, have allowed for an increasing number of people to live part or full‐time in highly desirable rural locations, particularly those proximate to larger urban areas. In this paper, we discuss the historical and current trends of amenity migration in Kittitas County, proximate to Seattle, Washington, on the eastern slope of the Cascade Mountains. Drawing upon perspectives shared in 80 interviews with key informants and community members about community wellbeing in three towns, we discuss the implications of amenity migration for the perceived quality of life of both longer‐term residents and newer community members. Additionally, the setting and scope of this research allows for comparison between high‐amenity rural communities with larger recreation economies, and adjacent less—amenity‐based rural communities. Findings indicate that amenity migration continues to evolve and impact community wellbeing, primarily via community cultural changes and socioeconomic and housing inequality. However, there are nuanced geographical and longitudinal differences in the impacts of amenity migration. Additionally, participants perceived an increase in amenity migration patterns and impacts in the years following the COVID‐19 pandemic. To conclude, we discuss ongoing and potential initiatives that may help support community wellbeing, as well as possibilities for further improvements in policy and planning to equitably increase the quality of life for all residents.