What If Toronto's Waterfront Was Developed Differently?

The Actual History

Toronto's relationship with its waterfront has been a complex saga of industrialization, transportation priorities, and delayed revitalization efforts. Before European settlement, the area that would become Toronto featured a natural harbor sheltered by the Toronto Islands. The British established the Town of York in 1793, with the waterfront serving as a crucial commercial port. Throughout the 19th century, the harbor evolved into an industrial zone as railways were built along the shore, creating the first physical barrier between the city and Lake Ontario.

The early 20th century saw Toronto's waterfront dominated by industrial uses, with factories, warehouses, and shipping facilities lining the shore. Following World War II, North American cities embraced automobile-centric development, and Toronto was no exception. The defining moment for Toronto's waterfront came in the 1950s and 1960s with the construction of the Gardiner Expressway, an elevated highway that created a permanent concrete barrier between the city and its lake. Completed in 1966, the Gardiner solidified a transportation planning philosophy that prioritized vehicular movement over pedestrian access and urban connectivity.

Simultaneously, extensive lakefill operations expanded the shoreline southward, creating new industrial lands and later the Toronto Islands Airport (now Billy Bishop Toronto City Airport). By the 1970s, Toronto's industrial waterfront began declining as manufacturing shifted away from urban centers. The port functions diminished, leaving vast tracts of underutilized and contaminated post-industrial land along the shore.

The 1972 "Harbour City" proposal by developer Robert Campeau envisioned a residential community on the waterfront but was rejected following citizen opposition led by Jane Jacobs and others. This marked the beginning of decades of unrealized waterfront plans. The 1988 Royal Commission on the Future of the Toronto Waterfront (known as the Crombie Commission) recommended comprehensive environmental restoration and public access improvements, but implementation was limited.

In 1999, Toronto's bid for the 2008 Olympic Games catalyzed renewed attention to the waterfront, despite the bid's ultimate failure. This led to the creation of Waterfront Toronto in 2001, a tri-government agency tasked with overseeing revitalization efforts. The organization has since managed several successful projects, including the award-winning Sugar Beach, HTO Park, and the revitalization of Queens Quay Boulevard with improved public spaces and transit access.

However, progress has been incremental and often politically contested. The eastern port lands remained largely underutilized until the 2010s when flood protection and naturalization projects began. The western waterfront continues to struggle with the imposing presence of the Gardiner Expressway, despite recurring debates about its potential removal or burial. Recent developments like CityPlace have added thousands of condominium units near the waterfront, though critics argue these developments lack community amenities and prioritize density over livability.

By 2025, Toronto's waterfront revitalization remains an ongoing project, with significant progress in certain areas but continuing challenges in creating a cohesive, accessible shore. The legacy of prioritizing infrastructure over public space continues to shape the city's relationship with Lake Ontario, making Toronto's waterfront a patchwork of successful revitalization projects alongside persistent barriers and underdeveloped zones.

The Point of Divergence

What if Toronto had rejected the automobile-centric waterfront development model in the post-war period? In this alternate timeline, we explore a scenario where Toronto made fundamentally different choices about its waterfront in the pivotal decades following World War II, setting the city on a dramatically different urban development trajectory.

The point of divergence centers on the decision-making process around the Gardiner Expressway in the early 1950s. In our timeline, Metropolitan Toronto Chairman Frederick Gardiner (after whom the expressway was named) championed the elevated highway as essential infrastructure for the growing city. But what if a different vision had prevailed?

Several plausible alternatives could have shifted Toronto's development path:

First, the city might have embraced a boulevard model instead of an elevated expressway. In this scenario, urban planners influenced by European models could have convinced municipal leaders to adopt a wide, tree-lined lakeshore boulevard with integrated public transit—similar to Chicago's Lake Shore Drive but with dedicated streetcar lanes. This approach would have maintained transportation capacity while preserving visual and physical connections to the lake.

Alternatively, Toronto could have followed the example of waterfront cities like San Francisco, which eventually removed planned waterfront expressways following citizen opposition. Perhaps Jane Jacobs, who later successfully opposed the Spadina Expressway, might have arrived in Toronto earlier (instead of 1968) and mobilized effective resistance against the Gardiner plans.

A third possibility involves different federal priorities. If the Canadian government had established a national urban policy emphasizing public transit and waterfront preservation in the immediate post-war period, Toronto might have received funding earmarked for subway expansion and waterfront preservation rather than expressway construction.

The most compelling scenario combines elements of these alternatives: In this alternate timeline, a coalition of forward-thinking planners, concerned citizens, and progressive politicians successfully advocated for a "Toronto Waterfront Vision" in 1953. This comprehensive plan prioritized public transit (expanding the young subway system with a waterfront line), created continuous public access to the shore, preserved industrial functions in designated areas, and developed mixed-use neighborhoods with direct water access. Instead of the elevated Gardiner Expressway, this plan implemented a tunnel for through traffic in critical sections while maintaining a human-scaled surface transportation network.

This visionary approach, occurring just as Toronto was beginning its post-war boom, would have fundamentally altered the city's relationship with Lake Ontario and set a different precedent for North American waterfront development at a crucial moment in urban history.

Immediate Aftermath

Transportation System Evolution

The immediate impact of Toronto's alternative waterfront vision would have been most visible in its transportation infrastructure. Without the elevated Gardiner Expressway creating a concrete barrier, the city's connection to the lake would have remained intact during the crucial growth years of the 1950s and 1960s.

The "Downtown Waterfront Line," a proposed east-west subway or light rail corridor running parallel to the shore, would have begun construction by 1957, connecting the existing north-south Yonge subway line to the waterfront. This transit-first approach would have established a pattern of development oriented around public transportation nodes rather than highway access points. Key waterfront destinations would have developed around transit stations rather than parking facilities.

For necessary through traffic, sections of belowground expressway would have been constructed by 1963, but with significantly smaller footprints than the actual Gardiner. The surface would have featured a tree-lined boulevard with dedicated transit lanes, cycling infrastructure, and generous pedestrian spaces—an approach that maintained transportation capacity while preserving the urban fabric.

Metropolitan Toronto Chairman Frederick Gardiner, rather than being remembered for an elevated expressway, would have become associated with this innovative transit-oriented waterfront approach. In a 1959 speech in this alternate timeline, Gardiner proclaimed: "Toronto is showing North America that a modern city need not sacrifice its waterfront to the automobile. We are building a transportation system that serves the city, rather than dividing it."

Industrial Transformation and Economic Impact

Toronto's industrial waterfront would have undergone a more managed transition beginning in the late 1950s. Rather than allowing unplanned industrial decline, the city's "Working Waterfront" program would have designated specific areas for continued port and industrial functions while gradually transitioning others to mixed-use development.

The Toronto Harbour Commission, working with the newly established Waterfront Planning Authority, would have implemented stricter environmental controls on waterfront industries by 1960, well ahead of broader environmental regulations. This forward-thinking approach would have reduced contamination issues that later plagued redevelopment efforts in our timeline.

Economically, this approach would have generated significant construction employment through the 1960s while establishing Toronto as a center for urban planning innovation. International delegations began visiting Toronto by 1965 to study its waterfront approach, creating a consulting industry for Canadian urban planners and boosting tourism.

Real estate values along the accessible waterfront would have risen more rapidly than in our timeline, generating tax revenue that partially offset infrastructure costs. A 1962 economic impact study in this alternate timeline estimated that the accessible waterfront generated 15% more economic activity than projected under an expressway-dominated model.

Early Waterfront Communities

By the mid-1960s, the first new waterfront neighborhoods would have emerged. "Harbour Square," located near the present-day Harbourfront Centre, would have been developed as a demonstration project featuring mid-rise, mixed-income housing with ground-floor retail and cultural spaces. Unlike the later high-rise condominium developments of our timeline, these communities would have featured diverse housing types, numerous small parks, and direct water access.

The Toronto Islands would have remained primarily residential, without the airport expansion that occurred in our timeline. The island community, rather than fighting for its existence against airport expansion, would have been incorporated into the waterfront vision as a model car-free neighborhood connected to the mainland by improved ferry service and potentially a pedestrian tunnel.

Mayor Nathan Phillips, who in our timeline oversaw the construction of Toronto's new City Hall, would have embraced the waterfront vision as complementary to his efforts to modernize Toronto. In a 1965 interview, he noted: "Our new City Hall represents Toronto's aspirations for the future, but our new waterfront represents how we're actually living those aspirations daily. We're creating a city where people can live, work, and play along the lake that has always defined Toronto."

Cultural and Recreational Revival

The waterfront's accessibility would have sparked a cultural renaissance along the shore by the late 1960s. The "Harbour Arts District" would have emerged organically around Queen's Quay, with adaptive reuse of industrial buildings for studios, galleries, and performance spaces—similar to New York's SoHo but with direct water access.

A continuous waterfront trail system would have been completed by 1968, connecting the Humber River in the west to the Don River in the east. This early investment in recreational infrastructure would have established a public expectation of waterfront access that shaped all subsequent development decisions.

Annual festivals celebrating Lake Ontario and Toronto's maritime heritage would have begun by 1967 (Canada's centennial year), creating traditions that reinforced the city's identity as a waterfront community. These cultural developments would have occurred decades earlier than similar initiatives in our timeline, allowing them to become deeply embedded in Toronto's civic identity before the development pressures of later decades.

Long-term Impact

Toronto's Global Urban Identity

By the 1980s, Toronto's alternative development path would have fundamentally altered its global reputation and self-image. Rather than being known primarily as a financial center with impressive banking towers, Toronto would have developed an international reputation as "The Livable Waterfront City," regularly topping quality-of-life rankings decades before it began doing so in our timeline.

This reputation would have attracted a different profile of international investment and immigration. While still drawing financial services and becoming a banking center, Toronto would have also emerged as a global hub for urban sustainability innovation, with numerous international organizations establishing headquarters along its accessible waterfront by the 1990s.

The United Nations Environment Programme would have opened its North American headquarters in Toronto in 1988, drawn by the city's successful integration of environmental restoration with urban development. This would have positioned Toronto at the center of early climate adaptation discussions for coastal cities, creating an expertise cluster that generated significant intellectual and economic capital.

Tourism patterns would have evolved differently, with Toronto's waterfront becoming its primary attraction rather than the CN Tower (which would likely still have been built, but would have been integrated into a more cohesive waterfront district). By 2010, tourism revenue would have been approximately 30% higher than in our timeline, with longer average visitor stays focused on the waterfront experience.

Environmental Leadership and Innovation

The preservation of Toronto's connection to Lake Ontario would have fostered a stronger environmental consciousness throughout the region. The Don and Humber River valleys would have been prioritized for restoration decades earlier, with naturalization projects beginning in the 1970s rather than the 2000s.

By 1985, Toronto would have implemented one of North America's first comprehensive urban stormwater management systems, using waterfront parks as functional infiltration zones while creating public amenities. This approach would have significantly improved Lake Ontario water quality along Toronto's shoreline, allowing for swimming beaches throughout the waterfront by 1990.

The Port Lands would have undergone remediation and naturalization beginning in the 1980s rather than the 2010s, creating the naturalized mouth of the Don River decades earlier. This early adoption of urban ecological restoration would have established Toronto as a pioneer in blue-green infrastructure, attracting environmental technology companies and research institutions.

Climate resilience would have been incorporated into waterfront planning much earlier than in our timeline. By 2000, Toronto would have implemented comprehensive flood protection and climate adaptation measures along its shore, making it a model for coastal cities facing rising water levels and increased storm activity.

Urban Form and Housing Patterns

Toronto's urban form would appear markedly different by the 2020s. Without the Gardiner creating a psychological barrier, development would have proceeded more evenly toward the lake, creating a gradual transition in building heights rather than the abrupt wall of condominiums that characterizes parts of Toronto's waterfront today.

The city would have maintained a more diverse housing stock along the water, with policies implemented in the 1970s requiring mixed-income development in all waterfront communities. This would have mitigated (though not eliminated) the housing affordability challenges that Toronto faces in our timeline, as approximately 30% of waterfront housing would be permanently affordable through community land trusts and non-profit housing corporations.

The downtown core would have extended more naturally to the waterfront, with a finer-grained street network connecting the financial district to the lake. This improved connectivity would have created a more walkable city with numerous small public spaces rather than a few large ones, following the urban design principles that Jane Jacobs advocated.

Building height and density would still have increased over time, but with more human-scaled podiums and setbacks preserving sunlight access to public spaces. By 2025, Toronto's skyline would feature a more gradual transition from the high-rise downtown to mid-rise waterfront neighborhoods, rather than the abrupt contrast seen in our timeline.

Economic Structure and Innovation

Economically, Toronto would have developed a more diverse base beyond financial services and real estate. The accessible waterfront would have fostered innovation clusters in urban technology, environmental services, and creative industries beginning in the 1980s.

The "Toronto Waterfront Innovation District," established in eastern waterfront areas that remained industrial into the 1990s in our timeline, would have emerged by 1995 as a hub for technology companies seeking urban amenities and quality of life to attract talent. This would have positioned Toronto to compete more effectively with San Francisco, Boston, and other technology centers during the early internet boom.

Manufacturing would have retained a presence in specialized zones along the eastern waterfront, evolving toward higher-value production rather than disappearing entirely. The "Made on the Lake" initiative would have supported small-scale urban manufacturing in designated areas, preserving blue-collar employment opportunities within the city core.

By 2025, Toronto's economic base would be noticeably more diverse than in our timeline, with less dependence on financial services and real estate development. The city would have weathered economic downturns more successfully due to this diversification, experiencing less dramatic housing market volatility.

Transportation Network Evolution

Toronto's transportation network would have evolved very differently without the Gardiner's dominance. The waterfront transit line, expanded and modernized through the decades, would have become the backbone of an extensive light rail network by the 1990s, connecting to regional rail services and subways.

The city would have implemented progressive transportation policies decades earlier, including pedestrianized areas along the central waterfront by the 1980s and comprehensive cycling infrastructure by the 1990s. By 2010, approximately 35% of downtown trips would occur by active transportation (walking or cycling), compared to roughly 15% in our timeline.

Regional transportation connections would have developed with the waterfront as a key hub. GO Transit, the regional transportation system, would have established its main downtown terminal at the foot of Bay Street by 1975, integrating seamlessly with the waterfront transit line and creating a true multi-modal hub decades before the Union Station revitalization of our timeline.

By 2025, Toronto would have a transportation modal split more similar to Copenhagen or Amsterdam than to other North American cities, with public transit, cycling, and walking accounting for over 70% of trips in the central city area.

Regional Planning Impact

Perhaps most significantly, Toronto's alternative waterfront vision would have influenced regional development patterns throughout the Greater Toronto Area. The success of the waterfront model would have created political support for more transit-oriented development throughout the region.

Suburban communities around Toronto would have developed more compact town centers connected by regional rail rather than the highway-oriented sprawl that characterized actual development. The Greenbelt Plan, which protects land around Toronto from development, would have been implemented in the 1980s rather than 2005, preserving significantly more agricultural land and natural areas.

By 2025, the Greater Toronto Area would have a more polycentric structure, with density clustered around transit nodes throughout the region rather than concentrated downtown with sparse suburban development beyond. This would have created a more sustainable growth pattern with reduced commute times, lower infrastructure costs, and preserved natural systems.

Expert Opinions

Dr. Jennifer Wong, Professor of Urban Planning at the University of Toronto, offers this perspective: "The decision to build the Gardiner Expressway was emblematic of a particular moment in North American urban development—one that prioritized vehicle movement over human experience and environmental considerations. In an alternate timeline where Toronto rejected this approach, the city would likely have developed a very different urban form and identity. The psychological impact of maintaining a connection to Lake Ontario cannot be overstated; it would have fundamentally altered how Torontonians perceive their city and influenced countless subsequent development decisions. While we've made progress in recent decades reconnecting with our waterfront, we're still working to overcome the physical and psychological barriers established during the 1950s and 1960s."

Marcus Rodríguez, Senior Fellow at the Global Waterfront Cities Institute, suggests: "Cities that maintained their connection to their waterfronts during the mid-20th century—like Vancouver, which rejected waterfront freeways, or European cities that prioritized public space along their shores—have consistently demonstrated stronger economic resilience, higher quality of life metrics, and better environmental outcomes than those that surrendered their waterfronts to transportation infrastructure. In an alternate timeline, Toronto could have become North America's premier waterfront city decades earlier, potentially altering the continent's urban development paradigm during a crucial period. The opportunity cost of Toronto's actual waterfront development cannot be calculated simply in land values or tax revenue—it represents a fundamental shift in urban identity and function that would have positioned the city very differently in the global urban hierarchy."

Dr. Aisha Chen, Environmental Historian and author of "Contested Shores: North American Waterfront Transformations," provides this analysis: "What makes Toronto's waterfront history particularly poignant is that the city came so close to different outcomes at several key junctures. The Harbour City proposal of 1972, the Crombie Commission recommendations in 1988, and numerous other plans demonstrated an understanding of the waterfront's potential that simply couldn't overcome the momentum of earlier decisions. In an alternate timeline where those earlier decisions went differently, Toronto might have created a model for post-industrial waterfront transformation that other cities would have emulated. Instead, Toronto has often found itself implementing ideas pioneered elsewhere, decades after they might have originated here. The environmental implications alone would have been profound—earlier remediation of industrial contamination, more natural shoreline treatments, and integrated stormwater management would have significantly improved Lake Ontario's ecosystem health throughout the western basin."