The City of Springfield, Massachusetts is one of the largest cities in western Massachusetts, and was established on the Connecticut River for trading and as a fur-collecting post. In 18th and early 19th century, it experienced an industrial boom and became a regional financial center. Springfield became a major railroad center and grew to become the regional center for banking, finance, and courts. However, in mid-19th century Springfield suffered due to the flooding of the Connecticut River and the disinvestment in industry. These resulted in an urban sprawl as people started moving away from heart of the city. Now, once again, the city is trying to revitalize its downtown and neighboring areas to attract people by improving different types of social and cultural amenities. In this thesis, the author studies the relation of the city with its natural asset "The Connecticut Riverfront" which can be a great place to attract people towards the heart of the city. The author has also researched the various reasons causing this natural asset to be underutilized for several years. In addition, the author also explores the possibilities of connecting the Springfield downtown to the riverfront, providing safe and undisturbed access mainly to pedestrians, physically challenged people, and bike riders. Research shows that the existing transportation paths are the major barriers discouraging people from reaching the riverfront. In order to overcome this problem, a design solution is proposed including a safe, pedestrian-friendly link from the downtown area to the riverfront mitigating all the transportation paths such as highway, high speed traffic roads, and railway tracks. The proposed link will give encouragement to local artist and will also aim to boost local businesses by providing sites for museums, exhibitions, art galleries, food courts, and retail shops. This structure will not only improve the accessibility but it will also provide public open spaces where people can gather for various activities and can also enjoy the scenic view of the riverfront. In Addition, local people can also enjoy the water viewing restaurant and bar overlooking Connecticut River. Lastly, this connecting link lays the foundation for further development of the riverfront area due to increased accessibility to this asset.