Some people may think that Toronto is like Lego Batman (it only works in black and very dark grey) but amongst the concrete and glass of the business district and the green of parks and playgrounds strewn all around town, there are various interesting architectural icons and historical gems to check out. Plus, you can do this tour by foot any time of year, no matter the weather! So, to learn about our city’s past, present and future, get your walking shoes on and check off our list of 20 Cool Buildings to Discover in Downtown Toronto.

Cool Buildings of Toronto — Tourist Attractions

1. CN Tower
Well, of course, we have to start with the big kahuna of the Toronto skyline. At the tallest freestanding building in North and South America, you take a fast elevator up (which you feel in your tummy, like a reverse rollercoaster!) to an observation deck with 360 degrees of spectacular city views. Hot tip: Eat a fancy meal at the revolving restaurant to get a free ride up!

2. Rogers Centre
To me, this entertainment venue will always be the SkyDome! Home to the Toronto Blue Jays (currently Canada’s only pro baseball team), it’s one of the first multi-sport stadiums designed with a retractable roof, and it also hosts special events and concerts throughout the year. Hot tip: we’ve got oodles of family tips for going to games here!

A lovely night at the “SkyDome” with a view of the famous CN Tower. Photo credit: Melissa Mohaupt

3. St. Lawrence Market
The most delicious-smelling building on our list, it’s been a working food market since 1902. The building is so old that it was used as Toronto City Hall from 1845 until 1899 when they built what we now call “Old City Hall”. Don’t miss the peameal bacon sandwiches!

4. The Distillery District
A once-derelict group of industrial factories became a new neighbourhood hotspot when it was developed into a pedestrian village of condos, restaurants, stores and theatres. Thankfully, it has retained its vintage vibe, hosting events and a popular Christmas market.

5. John Street Roundhouse
Toot toot, calling all Thomas the Tank Engine fans! This former train garage is over 90 years old and is now home to the Toronto Railway Museum, Steamwhistle Brewery, and The Rec Room restaurant and indoor arcade. 

Roundhouse Brewery

The John Street Roundhouse and Steam Whistle Brewery, with the Rogers Centre. Photo Credit: Melissa Mohaupt

6. Harbourfront Centre
Head to Harbourfront for fun any time of year for events such as festivals and outdoor skating. Architecturally speaking, the Power Plant Contemporary Art Gallery is another excellent example of refurbishing an unused industrial building to the benefit of the city’s art patrons and visitors.

7. Hockey Hall of Fame
A bank built in 1885 became the Hockey Hall of Fame in 1993, and while many of the exhibits are located underground, the Esso Great Hall takes advantage of the impressive heritage space to create a cathedral to hockey, home to the Stanley Cup and all of the major NHL trophies.

8. Ontario Place
Once a bustling amusement park, this waterfront park is currently being redeveloped for future recreational uses, though there are still some concerts and events happening in warmer months. The most notable part of Ontario Place is the series of domed buildings that look like islands floating in Lake Ontario, which includes the IMAX movie theatre Cinesphere.

Cool Buildings of Toronto — Culture & Museums

9. Art Gallery of Ontario (AGO)
A recent renovation and addition of this world-renowned art gallery was designed by Toronto-born superstar architect Frank Gehry, with a glass atrium on the top level that resembles a big fish and an extremely photogenic central staircase.

AGO’s Galleria Italia. Photo Credit: Melissa Mohaupt

10. Royal Ontario Museum (ROM)
Another longstanding museum that has received a striking addition is the ROM, which looks like huge crystals attaching themselves to an old castle! The original building is no slouch either, though: the lobby retains its gorgeous mosaic ceiling and staircases that wind around tall totem poles.

11. Fort York National Historic Site
The City of Toronto recently announced that their historical museums now have free admission which gives you a great reason to head a bit west in the downtown core and find Fort York, hidden under the many towering condo buildings near the Gardiner Expressway.

12. Roy Thomson Hall
Home to the Toronto Symphony Orchestra, this breathtaking modern round concert hall is often recognized by film & TV buffs for its many on-screen appearances, such as X-Men and The Boys. Even better, you can check it out from the inside as you take in one of TSO’s fantastic kids’ concerts!

13. Elgin and Winter Garden Theatre
The Ontario Heritage Trust runs regular tours of this double-decker theatre — the last one running in the world! — and various performances run throughout the year. The upstairs Winter Garden even has a leaf-decorated ceiling and they also say it’s haunted.

14. Massey Hall
Having recently completed an extensive renovation, Toronto’s best-known music venue is better than ever… and it already had perfect acoustics! It’s a favoured venue by artists throughout the music business, including Canadian legends Neil Young and the late-great Gordon Lightfoot.

Cool Buildings of Toronto — Hospitality & Transportation

15. Union Station
Another institution that has been under renovation for a lonnng time, Union Station has recently opened new retail and restaurants for its daily throngs of commuters, but the Grand Hall is still its old majestic self.

Union Station

The intricate stonework on the ceiling of Union Station’s Great Hall. Photo credit: Melissa Mohaupt

16. Royal York Hotel
Just across the street from Union Station, the only hotel to make this list is the Royal York for its sheer grandeur and luxurious old-school lobby.

Cool Buildings of Toronto — Fascinating Architecture

17. Toronto City Hall & Old City Hall
Almost as recognizable as a Toronto symbol as the CN Tower, our city hall is so memorable that it’s now also the logo! It’s interesting to see the modern style clashing with the “old” city hall building that sits next door, which is now a courthouse.

Join the skating party at Nathan Phillips Square, or just watch from above at the Sheraton Centre Hotel. Photo Credit: Melissa Mohaupt

18. Gooderham Building (“Flatiron”) & Berczy Park
Did you know that our “flatiron” building is older than New York’s?! Theirs may be bigger but ours is just as pretty, and while you’re there, be sure to stop at Berczy Park just behind it to see the adorable dog-themed water fountain.

19. Ontario College of Art and Design (OCAD)
OCAD, or the Sharp Centre for Design, is a black-and-white box that seems to float in the air, held by coloured pillars. It was also featured on “The Amazing Race Canada” this season, where racers climbed up the poles (don’t try that in real life!). Hot tip: if you stand at the northeast corner of Dundas and McCaul and face kitty-corner (southwest), you can fit the CN Tower, OCAD and the AGO all in one photo!

20. Casa Loma
OK, Casa Loma isn’t technically downtown, but we had to include it… it’s a castle, for heaven’s sake! They run regular tours throughout the year and also host numerous events, such as high tea, concerts and events at Halloween and Christmas. Interesting tidbit: Casa Loma was designed by E.J. Lennox, who was also the architect on record for Old City Hall. Ask your kids about what they think are the differences and similarities between the two.

Smarten up with our list of Museum events in Toronto and the GTA here!