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The focus of this thesis is the creation of a series of architectural installations, bridges and gardens that link together via a pedestrian/bike path to connect the urban center of Main St. in Brattleboro, Vermont with the municipal park on the western end of town known as Memorial Park. This thesis argues that the vast majority of community interactions take place along the sidewalks of the urban downtown, and in certain centers of activity in and around the area, such as Memorial Park. Thus, these two places have been chosen to test whether architecture can be used to bridge the distance between two locations, and link them. Through an in-depth study of the town's network of pathways, traffic patterns, and sidewalk conditions, it was discovered that the main areas of community gathering have no safe method of connection except via automobile. However, the very nature of the automobile tends to isolate individuals and limit community interaction. Therefore, by combining the desire to increase a sense of community interaction, this thesis creates a community pathway that connects Main St and Memorial Park. The route will have a series of small outdoor architectural installations including a swimming hole, music amphitheater, and open-air movie theater, that will be linked via walkways and bridges along the Whetstone Brook that runs from west to east through the center of Brattleboro.