This report presents an urban planning and design proposal for downtown Holyoke, Massachusetts, in anticipation of a potential casino and entertainment complex being introduced into the city’s urban fabric. Recognizing the transformative impact such a development could have, the proposal addresses necessary changes to land use, human activity patterns, transportation systems, building reuses, and the historic canal network. Through comprehensive planning and design strategies, the proposal seeks to channel the energy and attention generated by the casino debate into the creation of a distinctive urban district that celebrates Holyoke’s past while accommodating its future. The study draws from Holyoke’s historical context and urban evolution, incorporating precedent research and case studies of similar development strategies. It envisions a revitalized downtown that embraces more than just a casino complex by enhancing the city’s historic assets—such as its canals, mills, and 19th-century architecture—while introducing a vibrant Urban Entertainment Destination. The resulting framework balances cultural preservation, economic opportunity, and thoughtful urban design, aiming to position Holyoke as a model for integrated and adaptive urban redevelopment.