Connecting green spaces, and providing meaningful and convenient pedestrian passage are two ideas that push sustainability, encourage community activity, and create a more enjoyable environment for the users. This is the thought process behind the proposal to redevelop the Minneapolis Chain of Lakes Regional Park. Currently all pedestrians walking through the park (from Lake Calhoun to Lake of the Isles) are forced underneath Lake St. on a single sidewalk that is only accessible near the North East corner of Lake Calhoun, and the nearest alternative crossing is a stop light located more than a block away. This research explores the different solutions that have been used to unite public spaces, and provide useful and convenient pedestrian trails. The park was initially designed as part of a system of parks that wind through the city of Minneapolis called the Grand Rounds, Horace William Shaler Cleveland was the designer, and his philosophy was to create a city that is a work of art. (Nadenicek, p.5). The park system is very successful for recreational purposes but could be updated to accommodate more utilitarian (non-recreational) trips. Manny cultural destinations around the park were not present when Cleveland designed the grand rounds and more meaningful and useful connections can be made to the neighborhood. A process of inventory and analysis will help determine the right solution to fit the site. The aim of this study is to provide updated connections to the neighborhood and motivate more people to walk or bike. Success of this will be determined by the number of pedestrians using the park system for non-recreational trips, and travel time from one end of the park to the other.