A History Buff’s Guide To Toronto


Lead Photo: Tiffany Shum

Take in Toronto’s story with our history buff’s guide. From charming neighborhood walks to luxurious historic hotel stays, discover the history and charm of Canada’s largest city.

Historic Stays

Check-in to one of Toronto’s oldest and most luxurious hotels and spend the night in history. From charismatic boutique styles with colorful pasts, to one of Canada’s grand railway hotels, you’ll have a stay to remember.

Gladstone House

The Gladstone was originally built in 1889 and is Toronto’s oldest continuously running hotel. Although it’s had many makeovers through the years, its original architecture has been largely preserved. Considered an arts and culture hub in the city, it features year-round artistic programming, exhibitions and live music.

The Broadview Hotel

The Broadview Hotel is a historic east end neighborhood landmark with a wonderfully colorful past. Originally built in 1891, it has been meticulously restored and reimagined as a 58-room boutique hotel and charismatic gathering spot. The hotel features (among other things) a stunning rooftop bar with views of the Toronto skyline.

Fairmont Royal York

Opening in 1929, the Fairmont Royal York retains many of it’s original features and has played host to royal guests, heads of state, celebrities, superstars of sport, and millions of others.

Featuring 28 floors, it is considered one of Canada’s grand railway hotels, and was briefly the tallest building in Toronto after it’s completion.

The Windsor Arms Hotel

Located in Yorkville, this neo-gothic style building was designed by architect Kirk Hyslop and originally built in 1927.

The Windsor Arms Hotel has been host to visiting royalty, aristocracy, stars of film and screen as well as heads of state and industry, and The Toronto International Film Festival was founded in the hotel in 1976.

Historic Bites

Spend the afternoon on the patio of one of Toronto’s oldest bars. With classic tavern fare and cold drinks, these loved neighborhood favorites are the ultimate destination for the hungry history buff.

The Wheatsheaf Tavern

The Wheatsheaf Tavern is considered Toronto’s oldest bar, and is the ultimate destination for classic tavern fare, live music, sports and whisky. Gracing the southwest corner of King and Bathurst as it has since 1849, this beloved neighborhood classic has been thoughtfully restored with new energy and life, while retaining the magic and character of its iconic status. 

The Black Bull Tavern

The Black Bull is one of the oldest bars in the city. However for several decades the building didn’t operate as a bar, so the claim of oldest goes to The Wheat Sheaf. The Black Bull has a huge patio directly on Queen Street West, perfect for people watching, dining on pub style fare or having a cold one with friends.

Historic Homes & Sites

Imagine what it would be like to host large, glamorous parties or discover Canada’s military history with a visit to one of Toronto’s historic sites. With carefully preserved period furnishings and architecture, these sites illustrate what life was like for some of Canada’s founding families.

Casa Loma

Casa Loma was first built in 1914 by financier Sir Henry Pellatt. The castle located in midtown Toronto, is now owned by the City of Toronto and is regarded as a treasured heritage landmark. 

Throughout the year you can tour the estate, gardens, and stables – now home to an antique car collection. The estate also offers fine dining, family entertainment, live music and hosts special events.

Spadina Museum: House & Gardens

Spadina Museum is conveniently located next to Casa Loma and is a dazzling mansion, showcasing the triumphs and tribulations of Toronto from 1900 to the 1930s. You are welcome to tour the estate and get a glimpse into this era through the perspective of the affluent Austin family and the people who worked in service within their home.

Fort York National Historic Site

Fort York is Canada’s largest collection of original War of 1812 buildings and 1813 battle site. Located in the heart of downtown Toronto, Fort York is open year-round and offers tours, exhibits, period settings, and seasonal demonstrations.

During the summer months, the site comes alive with the colour and pageantry of the Fort York Guard. Fort York also provides a wide variety of education programmes for groups of all ages.

Allan Gardens

The park originated from lands donated to the Toronto Horticultural Society by George William Allan in 1858, with the horticultural society officially opening a gardens there in 1860. The park and the gardens was initially known as the Horticultural Gardens until 1901, when it was renamed after Allan.

A fire ravaged and destroyed a three-storey pavilion at the park in 1902. However, a new conservatory building, the Palm House was later completed on the property in 1910.

Stroll Or Bike Through History

Whether exploring by bike or your own two feet, a tour of Toronto’s downtown neighborhoods is one of the best ways to discover the history and charm of Canada’s largest city.

University Of Toronto

The University of Toronto (U of T or UToronto) is a public research university in Toronto, located on the grounds that surround Queen’s Park. It was founded by royal charter in 1827 as King’s College, the first institution of higher learning in Upper Canada. Originally controlled by the Church of England, the university assumed its present name in 1850 upon becoming a secular institution.

The Distillery District

The pedestrian-only Distillery District, set in quaint 19th century buildings that once housed a large whiskey distillery, draws crowds to its cobblestone streets lined with hip indie restaurants, bars and boutiques. Art lovers come for the galleries, outdoor sculptures and dance, music and stage performances at the area’s several theatres. In December, the annual Toronto Christmas Market takes over the streets.


Cabbagetown is located on the east side of Toronto and is home to many largely untouched, heritage protected Victorian homes, and quaint alleyways.

The area also features two of Toronto’s oldest cemeteries, St. James Cemetery (1844) and the Necropolis Cemetery (1850). These are the final resting places for several important figures in Canadian history, including George Brown, Robert Baldwin and William Lyon Mackenzie.


Rosedale began when Sherrif William Botsford Jarvis, and his wife Mary settled on a homestead there in the 1820’s. For over a hundred years Rosedale has been home to many of Toronto’s wealthiest, most prominent citizens and their beautiful homes.

The area features Victorian, Georgian, Tudor, and Edwardian style mansions, many of which were built between 1860 to 1940 and are heritage protected.

Arts & Entertainment

Celebrate Canadian entertainment with a visit to some of the oldest theatres in North America. Or learn more about our culture and natural history with a visit to Canada’s largest museum. If art is on the agenda, you can discover European masterpieces such as Peter Paul Rubens’s The Massacre of The Innocents, or a vast collection by the Group of Seven, at the Art Gallery of Ontario.

Royal Alexandra Theatre

The historic Royal Alexandra is Toronto’s senior theatre, never having been converted to any other use and is the oldest continuously operating legitimate theatre in North America.

Since its opening in 1907, almost 3000 productions have played with a roster of stars that included, but not limited to: Orson Welles, Humphrey Bogart, Mary Pickford, John and Ethel Barrymore, and Fred and Adele Astaire. The Royal Alexandra was named a National Historic Monument in 1987, on its 80th birthday.

Elgin and Winter Garden Theatre

Built in 1913, the complex was the Canadian flagship of Marcus Loew’s legendary theatre chain. Designed by Thomas Lamb as a “double-decker” theatre complex, it contained the Winter Garden Theatre, constructed on top of the Elgin Theatre.

It’s home to the world’s largest collection of vaudeville scenery – hand-painted flats and drops dating from 1913. The Theatres are the last surviving Edwardian stacked theatres in the world.

Royal Ontario Museum

The Royal Ontario Museum is a museum of art, world culture and natural history. It is one of the largest museums in North America and the largest in Canada.

The ROM holds nearly 1 million objects of art and culture from around the world, dating from pre-historic civilizations to present day contemporary artworks. It has many large, permanent collections featuring thousands of works of art and cultural heritage including the largest collection of Chinese architectural artifacts outside of China.

Art Gallery Of Ontario

With a collection of more than 90,000 works of art, the Art Gallery of Ontario is among the most distinguished art museums in North America.

The AGO features European masterpieces such as Peter Paul Rubens’s The Massacre of The Innocents, a vast collection by the Group of Seven, as well as focused collections in Gothic boxwood miniatures and Western and Central African art. It also works with and features collaborations with museums from around the world.

As Toronto slowly re-opens, please check visitor information for Covid-19 rules and guidelines: https://www.toronto.ca/home/covid-19

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