Toronto's skyline and streetscapes are defined by iconic landmarks that tell the story of the city's evolution from a small colonial outpost to a global metropolis. As tour guides, we find that understanding the history behind these structures enriches the visitor experience, transforming these landmarks from mere photo opportunities into meaningful connections with Toronto's past. In this article, we'll explore the fascinating stories behind some of Toronto's most famous landmarks.
CN Tower: From Communication Hub to Tourism Icon
When the CN Tower opened in 1976, it claimed the title of world's tallest freestanding structure—a distinction it held for 34 years. Yet its origin story is far more practical than pursuing a world record.
The Railway's Legacy
The "CN" in CN Tower stands for Canadian National Railway, which built the tower to solve a very specific problem: by the 1960s, Toronto's growing skyline was interfering with radio and television signals. The railway company conceived a massive communications tower that would rise above all existing and future skyscrapers, ensuring clear broadcasting across the region.
Engineering Marvel
Construction began in 1973, and the engineering challenges were immense. Workers poured concrete continuously for 24 hours a day for eight months to create the tower's main shaft. The 335-meter concrete portion was built using a technique called slip forming, where concrete was poured into continuously moving forms. Once completed, the antenna was raised using one of the world's largest helicopters, a Sikorsky S-64 Skycrane.
Transformation to Tourism
What began as a communications solution quickly transformed into Toronto's primary tourist attraction. Today, the tower welcomes over 1.5 million visitors annually. The glass floor, installed in 1994, was among the first of its kind in the world, while EdgeWalk—an outdoor hands-free walk on a 5-foot ledge encircling the tower—launched in 2011 as the world's highest external building walk.
Interesting fact: The tower contains a time capsule sealed during construction, to be opened in 2076, its centennial year.
Casa Loma: A Medieval Castle Born of Fortune and Folly
Perched on a hill overlooking downtown Toronto stands Casa Loma, North America's only authentic full-sized castle—a Gothic Revival mansion that seems transported from European nobility but is actually the product of one Canadian financier's extravagant vision.
Sir Henry Pellatt's Dream
Casa Loma was built between 1911 and 1914 by Sir Henry Pellatt, a Canadian financier who made his fortune bringing electricity to Toronto and through various military and business ventures. Inspired by European castles he had visited, Pellatt commissioned architect E.J. Lennox to design his dream home, sparing no expense.
Unprecedented Luxury
The result was a 98-room castle featuring luxuries unheard of at the time: an elevator, central vacuum system, two vertical passages for pipe organs, and even one of Toronto's first private indoor swimming pools. The castle required thirty servants to maintain and cost approximately $3.5 million to build (equivalent to over $85 million today).
Financial Downfall
Sadly, Pellatt's dream home became his financial nightmare. Rising taxes, the decline of his business interests, and financial setbacks following World War I forced him to abandon Casa Loma in 1923, less than ten years after moving in. Pellatt and Lady Mary moved to their farm and later to a modest home, where he died in 1939.
Reincarnations
After Pellatt's departure, Casa Loma experienced various incarnations—briefly as a luxury hotel, then as a popular nightspot during Prohibition. The city seized the castle in 1933 for unpaid taxes, and it nearly faced demolition. Saved by the Kiwanis Club, which operated it as a tourist attraction for decades, Casa Loma is now managed by Liberty Entertainment Group and hosts everything from tours to weddings to film productions.
Interesting fact: Casa Loma has appeared in numerous films, including X-Men, Chicago, Scott Pilgrim vs. the World, and The Tuxedo.
St. Lawrence Market: From Town Hall to Culinary Hub
Consistently ranked among the world's best food markets, St. Lawrence Market's history mirrors Toronto's evolution from a frontier town to a metropolitan center.
Market Origins
The market's roots date back to 1803 when Lieutenant Governor Peter Hunter established a weekly Saturday farmers' market in the growing town of York (Toronto's original name). The official market building came in 1831, sharing space with the newly built City Hall—a practical arrangement where the building served civic functions on the upper floor while the ground level operated as a market.
Great Fire and Rebuilding
After Toronto's Great Fire of 1849 destroyed much of the neighborhood, including the market, it was rebuilt in 1851. The South Market building that visitors explore today dates from 1902, constructed in the grand Victorian tradition with a distinctive red brick facade and impressive interior dome.
Evolution of Purpose
Throughout its history, St. Lawrence Market has served multiple functions. Beyond food commerce, it has housed Toronto's first post office, city council chambers, a police station, and even a jail in the basement. The galleries above the market floor hosted social events and meetings of fraternal organizations.
Today's Market Experience
The present-day St. Lawrence Market comprises three buildings: the South Market (the main building with food vendors), the North Market (which hosts the Saturday Farmers' Market and Sunday Antique Market), and St. Lawrence Hall (built in 1850 and now housing various businesses). With over 120 vendors across these buildings, the market exemplifies Toronto's cultural and culinary diversity.
Interesting fact: Archaeologists working on the North Market redevelopment discovered the foundations of Toronto's first purpose-built jail, dating to 1824.
Distillery District: From Industrial Powerhouse to Cultural Village
The Distillery District stands as one of North America's finest examples of preserved Victorian industrial architecture, transformed from a spirits manufacturing complex into a pedestrian-only enclave of arts, culture, and dining.
Gooderham & Worts Legacy
The area began with a single windmill built in 1832 by James Worts and his brother-in-law William Gooderham to mill flour. After Worts' tragic suicide in 1834 (following his wife's death in childbirth), Gooderham continued the business and expanded into distilling to utilize excess grain. By the 1860s, Gooderham & Worts had grown into the largest distillery in the world.
Industrial Innovation
The complex's 40+ buildings, constructed primarily between 1859 and 1919, represent the era's most advanced industrial design. The site featured its own railway siding, coal-fired boilers, copper stills, and an elaborate network of buildings dedicated to every aspect of spirits production—from mashing and fermenting to bottling and shipping.
Prohibition and Decline
During Prohibition (1916-1927 in Ontario), the distillery remained operational by producing "medicinal" alcohol. After prohibition ended, the company merged with Hiram Walker in 1927, continuing production until 1990, when operations ceased, leaving the site abandoned for over a decade.
Cultural Renaissance
In 2001, developers Cityscape and Dundee Realty purchased the 13-acre site and embarked on a meticulous restoration, preserving the historic buildings while adapting them for modern use. The Distillery District reopened in 2003 as a pedestrian-only village dedicated to arts, culture, and dining, now hosting over 40 boutiques, galleries, restaurants, and performance spaces.
Interesting fact: Before its revival as a cultural center, the abandoned distillery was a popular filming location, appearing in over 800 films including Chicago, X-Men, and The Hurricane.
Fort York: Birthplace of Urban Toronto
While Toronto's modern skyline dominates the lakefront, it was at Fort York that the city began, with a garrison established to protect the settlement that would grow into Canada's largest metropolis.
Strategic Beginnings
In 1793, Lieutenant Governor John Graves Simcoe ordered the construction of a garrison on Lake Ontario's northern shore as a defense against potential American attacks. This military establishment formed the nucleus around which the Town of York (later Toronto) developed.
War of 1812 Battle
Fort York's defining moment came during the War of 1812 when American forces attacked York in April 1813. Outnumbered, British, Canadian, and Indigenous defenders retreated but not before detonating the fort's Grand Magazine. The massive explosion killed or wounded over 200 American troops, including their commanding general. The Americans occupied York briefly, burning government buildings and looting before withdrawing.
Reconstruction and Evolution
After the Americans departed, British forces rebuilt Fort York with more substantial defenses. Most of the structures standing today date from this 1814 reconstruction. The fort remained an active military installation until the 1880s and briefly returned to military use during both World Wars.
Urban Island
Perhaps the most remarkable aspect of Fort York's history is its survival despite Toronto's intense urban development. Once situated directly on the lakeshore, land reclamation and railway construction gradually cut the fort off from Lake Ontario. By the 20th century, the site was surrounded by industrial areas and, later, expressways and condominium developments. Despite these encroachments, Fort York remains as a National Historic Site, providing a tangible connection to Toronto's origins.
Interesting fact: The fort houses Canada's oldest surviving military structures and serves as the home base for the Fort York Guard, a historical reenactment program that demonstrates early 19th-century military life.
Old City Hall: Gothic Revival Grandeur
While it no longer serves as Toronto's municipal headquarters, Old City Hall remains one of the city's architectural treasures and a symbol of the city's ambition at the turn of the 20th century.
Architectural Statement
Designed by architect E.J. Lennox (who later designed Casa Loma), Old City Hall was constructed between 1889 and 1899 in the Romanesque Revival style. Its massive scale and elaborate stone carvings reflected Toronto's growing importance and self-confidence as a major Canadian city.
Construction Controversy
The building's construction generated considerable controversy due to cost overruns and delays. The original budget of $600,000 ballooned to nearly $2.5 million (approximately $75 million in today's currency). Lennox himself became embroiled in disputes with city officials, eventually embedding caricatures of critical city councilors and officials as stone faces on the building's exterior.
Near Demolition
After serving as the city's primary government building for 65 years, Old City Hall was nearly demolished in the 1960s to make way for the Eaton Centre shopping mall. Public opposition saved the structure, and it found new purpose as a courthouse, which it remains today.
Iconic Clock Tower
The building's most distinctive feature is its 103.6-meter clock tower, which dominated Toronto's skyline when completed. The four clock faces, each 6 meters in diameter, remain operational, and the tower's 5,443-kilogram bell still rings on the hour.
Interesting fact: Architect E.J. Lennox, frustrated by disputes over his fee, signed the building uniquely—if you look closely at the stone arches above the entrance, you can find "E.J. LENNOX ARCHITECT A.D. 1898" carved into the stonework.
The Royal Ontario Museum: A Century of Evolution
The Royal Ontario Museum (ROM) stands as Canada's largest museum of natural history and world cultures, with a distinctive architectural presence that reflects its evolution over more than a century.
From Department to Institution
The ROM's history begins in the late 19th century with departments of archaeology at the University of Toronto and the Ontario Provincial Museum. These collections merged in 1912 when the provincial government passed the Royal Ontario Museum Act, establishing the institution that opened to the public on March 19, 1914.
Architectural Layers
The original ROM building, designed in a Romanesque Revival style by Toronto architects Darling and Pearson, now forms just one part of a complex that has expanded multiple times. Major additions came in 1933 (the Queen's Park Wing), 1982 (the Terrace Galleries), and most dramatically in 2007 with the Michael Lee-Chin Crystal.
The Crystal Controversy
The ROM's most recognizable feature, the Michael Lee-Chin Crystal designed by architect Daniel Libeskind, generated intense debate when it opened. The angular, crystal-like structure of glass and aluminum dramatically contrasts with the museum's original heritage buildings. Libeskind described his design as inspired by the ROM's gem and mineral collection, creating an architectural intervention that some citizens loved and others loathed.
Collections Growth
From an initial 6,000 artifacts, the ROM's collections have grown to over six million objects spanning art, archaeology, and natural science. The museum houses everything from dinosaur fossils to Chinese temple art, Egyptian mummies to Canadian historical artifacts, making it a repository of global cultural heritage in the heart of Toronto.
Interesting fact: During World War II, the ROM stored many valuable artifacts from British museums in its basement to protect them from German bombing.
Experiencing Toronto's Historical Landmarks
These landmarks represent just a fraction of Toronto's rich architectural and historical heritage. On our Historical Toronto tour, we explore these sites and many others, providing context and stories that bring these structures to life. For visitors with limited time, we recommend prioritizing at least a few of these landmarks to gain insight into the city's evolution from colonial outpost to global metropolis.
While photographs capture these landmarks' visual appeal, understanding their history transforms them from mere backdrops into meaningful windows into Toronto's past. Each building, from Casa Loma's romantic folly to Fort York's strategic significance, adds a chapter to the story of how Toronto became the diverse, dynamic city it is today.
Have you visited any of these Toronto landmarks? What struck you most about their history or architecture? Share your experiences in the comments below!
