A Week in Toronto (Part 1)

DJ had a week-long business trip in Toronto recently and I tagged along. It was his first time in Canada and my first time in Toronto. In effort to reserve my leave for a proper vacation, I worked out of the hotel and various coffee shops all week while DJ was in the office and we explored the city on the weekends and in the evenings after work.

It was freezing (literally — it snowed on us several times) but we had a great time. Toronto is a fascinating city bursting with personality. We saw so much stuff in our week there, I’m splitting our trip highlights into two posts. Let’s get into part one.

Nathan Phillips Square

Named for a former mayor of Toronto (1955 to 1962), Nathan Phillips Square is hard to miss if you spend any time in the heart of the city. We passed by it many times walking to or from other city attractions. The water feature in front serves as an ice skating rink in the winter. We spent a significant amount of time staring at the giant sign (or in my case, snapping pictures). The lighting in the evening was always lovely, though I feel like photos don’t do it justice.

CN Tower

We didn’t actually ascend the 1,815 foot tower, but we did walk by it. It was much more massive up close than it appeared to be from elsewhere in the city, so it was definitely worth the closer look. Also, I’m not sure what it is with Toronto and giant color changing typographic signs, but there was a Canada sign located at the base of the tower that was very much like the Toronto sign in Nathan Phillips Square. It’s at a smaller scale, but otherwise very similar in style and lighting effects and was a popular photo spot. Fortunately, most people were super polite about taking turns standing near it for pictures, so it was easy to get a decent shot.


The PATH is one of Toronto’s more unique (and confusing) features. The core of the city can be traversed underground by an interconnected web of tunnels that resemble a shopping mall. There is a map for it, but it can be a little disorienting being underground with no natural directional indicators (like sun/moon).

We walked the PATH from Union Station to our hotel one evening after visiting the CN Tower. Since we were unfamiliar with it, it probably took us twice as long as it would have above ground, but it was a fun little adventure and a good way to stay warm. All the shops were closed when we were there, but the PATH itself stays open for use at all hours. If I were a local, it’s definitely a route I would spend time getting to know. Canada gets cooolllld.

St. Lawrence Market

Food vendors, produce, and fresh cut meats fill in the interior of the charming St. Lawrence Market. The vendors have turned the warehouse-like interior of this historic building into a brightly colored and playfully designed village of yum. I found the best approach for experiencing the market was to go in with the intent to graze — pick up an assortment of items from various vendors to pull together into a custom lunch spread.

As for me, I can happily recommend pierogis from European Delight, bagels from St. Urbain Bakery, and Portugese tarts from Churrasco. I enjoyed my treats to sounds of a live violinist in the lower level, at a table next to the mural pictured below.

Art Gallery of Ontario (AGO)

On Wednesday nights, the Art Gallery of Ontario opens its doors to the public for free from 6-9pm, which made it the perfect post-work destination in the middle of our trip. The exterior of the museum was designed by Frank Gehry and the interior contains nearly 95,000 works of art ranging from the Renaissance to today.

We didn’t manage to see it all, but we saw a lot of beautiful art, old and new, discovered new artists to admire, and enjoyed our time there immensely. It’s a beautifully set up gallery with a diverse collection.

Casa Loma

Casa Loma was technically the first attraction we visited, but it also includes the highest quantity of pictures in this post, so I thought it was a fitting way to end part one of our Toronto experience.

Casa Loma is a Gothic Revival style castle that currently serves as a historical museum. It was built in 1911 for Sir Henry Pellat to the tune of $3.5 million (closer to $93 million in today’s terms). He and his wife Mary lived there for less than ten years before becoming bankrupt. When your tastes move to you to do things like spend $10k (in 1911 dollars) per door on the four doors that lead to your conservatory, I suppose that’s not much of a surprise. We also learned that the house is a popular filming location and can be seen in numerous films and TV shows, including X-Men, Scott Pilgrim, Crimson Peak, Chicago, Billy Madison, and others.

We happened to be there the last weekend of an event they called “Imagine Dragons,” which had nothing to do with the popular band. Rather, they had parts of the house decked out with faux gargoyles, dragons, medieval-themed decor, and employees roaming the grounds dressed as knights. They had kid-oriented performances scheduled throughout the day, including the launching of a trebuchet in the backyard, which we watched from the top of a tower.

Not all the spaces in the castle were affected by the festivities, but it was sometimes a strange juxtaposition with the historical elements we saw (for example, a knight roaming back and forth in front of a medieval backdrop that was set up amongst the collection of early 1900s cars on display in the stables). I’m sure it was a hoot for the kiddos though. It was definitely a creative way to bring together history and play for a younger audience.

A highlight of our self-guided tour was a visit to the top of each of the towers on the house, particularly the open air one. A trek up a few dizzying flights of spiral staircases rewarded us with spectacular views of the city and surrounding areas (as well as frozen fingers and noses).

I do mildly regret not knowing about the Spadina house (above), a house-turned-museum that showcases life in the 1920s-30s, before our trip or we might have visited both it and Casa Loma that day. Curiosity about the house after seeing it from the tower spurred a quick look at Google Maps to find out what it was, but it was already too late in the day to go there. Maybe on another visit!

Thus concludes part one of our two part series about Toronto. We’ve saved our absolute favorite experiences for part two, so make you come back soon to check it out!

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