Ashley McDonough, Host of Walking in Place Podcast




Language: English

Area: Downtown

Theme: History & Culture

Accessibility: Family-Friendly, Fast Paced


We'll be walking in the Casa Loma/South Hill area, where you'll find some of the oldest streets (think: Ice Ages) and flashiest homes (think: medieval castles and private hospitals) this region has ever seen! Also, learn how to get your way with the city, and how not to keep your castle. Hint: it's fraud.


In between each stop on the audio tour you will hear 30 seconds of ambiance; these are sounds that were recorded in person on location. This tour was originally an episode of Walking in Place, a podcast series of audio walking tours in Toronto.

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When Toronto was first becoming settled, Davenport became a key path during the fur trade, and then was used by farmers to transport goods. It’s been worked on multiple times to accommodate streetcars, more lanes of traffic and bike lanes. When it first started being developed into a more formal road throughout the 1800s, they set up tollgates to help pay for it. One of them is still here- if you look at the northwest corner, there’s a little cottage- that’s now a museum called the Tollkeeper’s cottage.


From what I understand, the tollkeepers would live at the tollgate during their contract, which is why it’s a cottage rather than just a booth. It’s a museum now, and you can see the living quarters inside. 

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STOP 2: 

Next we head to the Nordheimer Ravine. There’s an entrance off of St. Clair Ave. W., east of West Hill Park. The ravine is named after Samuel Nordheimer, whose estate used to include the ravine as well as some of the land east of it. He named his estate Glen Edyth, after his wife, Edyth (a Glen is a type of valley). He and his brother ran a successful piano importing business, and eventually branched out into music publishing- basically owning the rights to publish the sheet music of certain songs or artists. 

STOP 3: 

Walk eastward through the ravine, through Winston Churchill Park towards the big building with the tall staircase up closer to St. Clair.


Why is this here?


It’s the portal building to the St. Clair Reservoir, which is right below this park. A path starts at the base of the staircase- follow it East until you get to Russel Hill Rd., then walk south on Russel Hill and enjoy the pretty houses as you walk downhill.

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STOP 4: 

Turn right onto Poplar Plains Rd., a historic First Nations trail. Keep walking until you reach Poplar Plains Crescent, and take a little detour through the Republic of Rathnelly if you feel like it. This tiny neighbourhood tried to secede from Toronto (and Canada!) in protest of changes proposed by the Spadina Expressway proposal in the 60s.


They’re pretty quirky - they crowned their own queen and voted in a poodle for mayor. The city honoured this history in 2012 by adding “Republic of Rathnelly” to their street signs, as well as renaming some of the streets in the area after early members of the community. 

STOP 5: 

Turn left on Cottingham St. and keep walking onto Cottingham rd. until it meets Davenport. Davenport is one of the oldest streets in the city. It’s kept a lot of its original shape- between Avenue and Weston Rd. it follows its original path, which is why it’s so curvy. Prior to the arrival of settlers, it was used as a portage trail for the city’s First Nations peoples, connecting the Don river to the Humber river. I read that it had been used by humans this way since the late ice ages! Between Avenue and Weston rd it actually follows its original path, which is why it’s so curvy. This area is also the shoreline of Lake Iroquois- which is what Lake Ontario used to be before it receded further south. So the whole city below is actually at the bottom of a historic lake.

STOP 6 & 7: 

Keep walking east on Davenport until you get to Walmer Rd. Turn right and walk up the hill until you get to the castle.


You can’t go in right now, but you can see some of the gardens from the parking lot. Walk over to the stables and Casa Loma parkette north on Walmer Rd. Apparently during World War II the stables housed a secret research labto develop a sonar device called ASDIC. City counsellors didn’t even know about it!

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STOP 8 & 9: 

Walk east on Castle View rd. towards Spadina (pronounced Spa-deen-ah) House. This was the home of William Warren Baldwin, who named it after what he thought the Ojibwe were calling Spadina rd. (the actual word is “Ishpadinaa”).


Funnily enough, the reason Spadina is such a straight line to the lake from this area is because it used to be Baldwin’s driveway. There’s a little park in between Spadina House and Casa Loma.


At the Southmost point are the Baldwin steps, where you can get a beautiful view of the city. At the bottom of the steps, you can see the Ojibwe spelling of Ishpadinaa on the Spadina street sign. Similarly, some of the Davenport street signs in this area also say “Gete-Onigaming”.


Depending on how long you may stop to look at things, this walk should take about an hour. It’s quite hilly and steep in some places, so be aware of that. 

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Depending on how long you may stop to look at things, this walk should take about an hour. It’s quite hilly and steep in some places, so be aware of that.

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