This Master’s Research Project (MRP) examines landscape connectivity strategies for the ravine system in the City of Toronto, CA. A workshop with natural environment specialists from the City of Toronto was organized to gather practitioner-based information as to which gaps should be prioritized in the ravine system. This GAP Analysis was complemented with a Geographic Information System (GIS) - based buffer analysis looking at connectable green spaces in close proximity to Environmentally Significant Areas (ESAs). Based on both the workshop and GIS analysis, 16 gaps were investigated through which 4 typologies were created. Interviews were then conducted with professionals from comparator cities: Edmonton (CA), Vancouver (CA), Minneapolis (US), Copenhagen (DK), and Stockholm (SW) to compare into how waterfront cities use policies, partnerships and design interventions to connect waterfront public lands. Based on interviews and additional policy scans, connectivity strategies were created for all 4 typologies as a means to improve landscape connectivity in the City of Toronto.