Part of a series on my favourite walking trails in Toronto.
Hey Toronto, remember to practice Physical Distancing during the COVID-19 pandemic! As part of its COVID-19 strategy, the City of Toronto may have closed some of the parks or other public facilities mentioned. Check with the City first.

And now on to the regular post …..

I’ve often wandered Toronto’s core, whether out for a noon stroll when I was working downtown, or just taking a roundabout way home when we lived near St. Lawrence Market. I thought it would be fun to put together a walking route of around 10 km that took in many of the sights, offered plenty of shopping, eating, and resting options, and provided a bit of tour through some of the historic parts of the city. I hope this route ticks those boxes for you.
Tip: I’ve included lots of links for some of the sights along this walk – check ahead to confirm opening times, and to find out about special shows or exhibits and things to do.
Length: About 10-12 km, depending on wanderings, so about 2.5 to 3 hours at a leisurely pace.
Surface: Paved.
Public Transit: I set this up to start and end at Nathan Philips Square, which is a block west from Queen Station on subway Line 1. You can also take the subway to Osgoode Station, also on Line 1 (on the University Ave side of the loop) and walk about 3 blocks east. Finally, you could adjust the walk to follow the loop shown but start/stop at Union Station, if you are coming in by GO train.
Route:
Starting at Nathan Philips Square, in front of the Toronto sign, head south-east towards Bay Street, and follow Bay south through the financial district to Front Street. Turn east on Front (left) and walk towards Yonge Street, passing the Hockey Hall of Fame. Continue east on Front Street past Berczy Park, crossing Church Street and continuing to Jarvis Street by the St. Lawrence Market.
Turn north on Jarvis and walk up to King Street, then turn west on King. You can cut through the gardens at St James Park if you’d like, or just keep going along King to Church Street. Turn north (right) on Church and continue up to Queen Street. Turn west (left) on Queen and continue to Yonge Street. Turn north (right) and walk up Yonge past Dundas Square, Ryerson University, and College Park, to reach Wellesley Street. Turn west (left) on Wellesley for about 50m, then turn north (right) onto St. Nicholas Street. Follow St. Nicholas north to Charles Street. Turn east (right) and return to Yonge Street, then turn north (left) and go up Yonge to Bloor Street.
Turn west (left) on Bloor and continue to Bay Street, crossing to the west side. Turn north on Bay and walk up to Cumberland Street. Turn west (left) on Cumberland and walk through Yorkville to Avenue Road. Turn south (left) on Avenue and walk down to Bloor. Cross Avenue and then cross Bloor, to reach the south-west corner by the Royal Ontario Museum. Continue west on Bloor to the gates marking the entrance to the Philosopher’s Walk, just west of the ROM.
Follow Philosopher’s Walk (fun fact – Philosopher’s Walk follows the ravine of the now-buried Taddle Creek) south to Hoskin Avenue. Cross Hoskin and then turn west (right) for about 50m to Tower Road on the University of Toronto campus. Turn south on Tower road and follow it through the arch at Soldier’s Tower. South of the Tower, follow Kings College Circle south and west and then cut west through the campus to reach the corner of St. George and Russell Street. Follow Russell Street west to Spadina Circle, then turn south on Spadina to reach College Street. Cross College and then Spadina to reach the south-west corner, and then continue west on College to reach Augusta Avenue. Turn south (left) down Augusta into Kensington Market. At Baldwin Street, turn east (left) and continue a few meters to reach Kensington Street. Turn south (right) and follow Kensington to Dundas Street.
At Dundas, turn east (left) and follow it, crossing Spadina in Chinatown. Continue on Dundas to Beverley Street, crossing to the south-east corner by the Art Gallery of Ontario. Turn south on Beverly and walk down to Grange Park. Enter the Park and cut through past the Henry Moore sculpture to reach Stephanie Street. Turn east on Stephanie and then after a few meters turn south to walk through the little park at St. Patrick’s Market. Continue south to Queen Street. Turn east (left) on Queen and cross University Avenue to the north-east corner. Jog north on University a few meters to the gate into Osgoode Hall gardens, turning east and walking through the Gardens to emerge on the west side of Nathan Philips Square. Walk through the Square to take a selfie in front of the Toronto sign!
Sights:
There are too many sights along this walk to list them all. If you want public spaces then there’s Nathan Philips Square, Berczy Park‘s famous Dog Fountain, Yorkville Park, and Grange Park and a few more.

If you want famous/interesting buildings there’s the Old and New City Halls, Brookfield Place, St. James Cathedral, College Park, all of U of T, and plenty of others too.

If you want culture, there’s the Royal Ontario Museum and the Art Gallery of Ontario, not to mention the Hockey Hall of Fame.

And if you want shopping, there’s St. Lawrence Market, the Eaton Centre, Yorkville and the Mink Mile, Kensington Market, and the many shops along the route.

This walk was designed to tempt you with lots of sights, so I wouldn’t be surprised if you started out with the best of intentions to finish and got so distracted that you have to come back another day.

Also, this walk works in any season. I did it recently on a scorching July day, and being able to pop into places like the Eaton Centre for some AC cooling was really nice. Passing so many covered shopping areas like that also means that on a rainy or snowy day, you can duck out of the weather. Then again, like so many walks in Toronto, I think this would be at its best in early autumn, to catch the foliage in Queens Park and U of T, and to take advantage of the harvest foods at the markets. And finally, don’t forget that in winter, you can go skating on the outdoor rink at Nathan Philips Square. Really, any time of the year will work.
Food & Refreshment:
I set this up going anti-clockwise round the downtown core, which means you go by St. Lawrence Market near the start, a perfect place for breakfast or lunch or a snack. Going in this direction lets you pass through Kensington Market near the end, which is also a great spot for food plus it has lots of coffee joints, juice bars, and beer-and-alcoholic drink bars. In between, there are coffee shops, restaurants, ice cream parlours, bakeries, donut shops, food trucks, and more that cover the spectrum from quick takeaway to full service sit-down.

As far as restrooms and toilets are concerned, there are lots – Nathan Philips Square, St. Lawrence Market, the Eaton Centre, College Park, and Yorkville all have public facilities, and of course the many coffee shops and restaurants along the way provide lots of options.
One thing there isn’t a lot of is water fountains – there are ones in St. Lawrence Market and in the Eaton Centre, but other than that you may want to carry water with you. Of course, the many food/drink options along the way will tempt you if you’re thirsty, so staying hydrated shouldn’t be a problem.
Diversions:
- This whole route offers detours, distractions, and diversions. My advice is to use the marked route as a rough guide and just let your curiosity take over.
- That said, the two food markets (Kensington and St. Lawrence) are destinations in themselves for me, and so are the AGO, the ROM, and the Hockey Hall of Fame. I could spend hours at any of these places.
- From the St. Lawrence Market area, heading east a bit and taking in the Distillery District is good fun. There’s a great holiday market there in December, and some tasty food and shopping options year-round.
- Starting at about Carlton Street, and running north about a block east of Yonge along Church Street, the Village is a vibrant, fun, and colourful neighbourhood that’s Toronto’s spiritual home of Pride and its LGBTQ community. The annual Pride parade attracts hundreds of thousands of people of all ages and is centred along Church.
- A few blocks further east of the Village, along Parliament Street between about Gerrard and Wellesley, the Cabbagetown neighbourhood showed Toronto what we could do with our beautiful Victorian homes. It’s full of good shops and quiet little streets that are perfect for a stroll, and nearby Riverdale Park and the Riverdale Farm offer lots of things for kids to do.
- Yorkville covers several square blocks between Yonge Street and Avenue Road, and between Bloor and Scollard Streets. A hippie hangout in the 1960’s, today it’s full of high-end shops, art galleries, bars, restaurants, and some of the best people-watching in the city.
