This report explores the feasibility of establishing a bikeway along Reach 4 of the Connecticut River in Massachusetts, a section extending approximately 18 miles from the Holyoke Dam to the Connecticut border. Initiated by the Massachusetts Department of Environmental Management in partnership with the National Park Service and the Connecticut River Watershed Council, the Connecticut River Valley Program (CVAP) aims to develop a coordinated approach to the river’s protection and recreational use. Reach 4—bordered by seven urbanized communities—faces significant environmental and infrastructural challenges, including limited public access due to highways, dikes, and railways, as well as poor water quality and riverbank conditions. Prompted by the University of Massachusetts Regional Planning Studio and CVAP’s commitment to riverfront revitalization, this study investigates the potential for a bikeway that connects communities, enhances recreational access, and links with existing networks such as the 5 College Bikeway in South Hadley. The report also outlines the three main types of bikeways—bike routes, bike lanes, and bike paths—and emphasizes the importance of providing safe, convenient, and attractive routes for cyclists in this highly urbanized river corridor.