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  #1  
Old Posted May 4, 2026, 9:03 PM
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Canadian Holidays - Questions, Advice and Reviews

Seems like a good time to start a new thread as SSP is a good place to get insider advice from people on towns, cities and urbanism. Also allows others to share their perspectives and we won't have the debate on whether or not a thread belongs in a region or city thread vs the Canada forum.

Multiple cities can be discussed at once - so I'll start off with Toronto.

Heading there again for the third May in a row (hope to go to Montreal for the 2nd September in a row later this year) and looking for recommendations on places to explore that I might have overlooked. I've explored most of the downtown by foot, but I'll look to add the Beaches neighbourhood which I haven't been to yet, and like I did the first year I'll do the CN Tower, cause, come on, being on SSP who doesn't like a great view of an ever changing skyline. I've checked out the concert scene, and as with last year there really isn't much going on, which is a disappointment, so I might drop into a random live music club and hope for the best.

Also looking for good lunch/small plates type places - I've found social media is not your friend in this regard. Any photography, architecture or art exhibits worth checking out?

Also considering a day trip to Hamilton, but as I'll be walking and I don't want to bother with renting a bike or scooter I suppose I'll be limited to downtown and area, although I've heard the escarpment overlooking the city is nice.

I haven't been to Mississauga - is there a compelling reason to visit beyond the Marilyn towers?
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Old Posted May 4, 2026, 9:39 PM
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I don't know that I'd want to schlep out to Mississauga, unless you've exhausted things to do in Toronto.
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Old Posted May 5, 2026, 1:50 AM
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Also considering a day trip to Hamilton, but as I'll be walking and I don't want to bother with renting a bike or scooter I suppose I'll be limited to downtown and area, although I've heard the escarpment overlooking the city is nice.

I haven't been to Mississauga - is there a compelling reason to visit beyond the Marilyn towers?
There are stairways up the escarpment in several places in Hamilton. There is one just south of downtown.
https://www.alltrails.com/trail/canada/ontario/james-street-stairs

Downtown is pretty grungy at the moment, the roads are poor and the homeless/drug-user issue is rampant. If you have time, I'd recommend walking between the West Harbour and the Escarpment (basically James St. most of the way) - it's about 4 km, but will take you through many different kinds of neighbourhoods. The bus isn't a bad way to take a tour either, if you'd like to cover a bit more ground. The city has been building new paved walkways along the edge of the escarpment, but where the James St. Stairs are the options are more limited. If the weather is nice and you're interested in more of a hike than a walk, the Bruce Trail runs right through the city along the escarpment. The paths along the West Harbour waterfront are also getting attention, but a couple of parks (Bayfront and Pier 4) have been there since the early-1990s and now have large trees, and if you're really feeling adventurous there's a trail all the way along that part of the harbour that eventually goes under the bridges at the western end and emerges next to a giant wetland and on to Princess Point to connect to more rugged trails around Cootes Paradise and through the RBG and university lands. There are more on the north side of the wetland, but poor trail connections mean walking up to York Blvd. to access them. If you're taking the GO train to Hamilton, you'll probably be using the newer West Harbour station that has all-day service... the downtown station has bus service but the trains are rush-hour out of the city in the morning and back in the early evening.

In Mississauga, the Port Credit area is a decent visit, though Lakeshore Rd. is pretty busy. There are some nice parks and paved trails near the Credit River, and some good restaurants on Lakeshore. It's not very large but probably the part of Mississauga I know best (and the Lakeshore GO station is there, for easy connections eastward and westward)

Last edited by ScreamingViking; May 5, 2026 at 2:10 AM.
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Old Posted May 5, 2026, 5:10 AM
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/\ Thank you ScreamingViking- I'll check out the maps. As for Hamilton I'd be happy enough to stroll through downtown and the nearby historic neighbourhoods and then the trails. I wish the downtown was more of a destination, but alas it seems to be a common challenge in much of the western world We really need to figure out the poverty/addictions/social challenges thing but that's another thread or forum entirely..
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Old Posted May 5, 2026, 6:21 AM
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Regarding Toronto, not sure what you've seen in the city so you may have already explored some of these locations. But I'll add some specific stuff you may have missed.

For the Beaches, I'd recommend getting off the streetcar around Woodbine and walking east through the neighbourhood to the RC Harris building which is a fantastic location for architecture/photography. Kew Gardens is along the way (check out the dawn redwood trees) and will lead down to the boardwalk/beach. Some turn-of-the-century residential around there as well.

On the theme of the east end, more centrally located is the Cabbagetown neighbourhood with the necropolis cemetery and the grounds of Riverdale Farm. Further east across the Don River is Riverside (sort of a small town-y Queen W vibe - tight Victorian residential). Riverdale north from there or Leslieville further east. The Danforth/Greektown is decent - lots of restaurants.

Distillery District with Corktown common, Biidaasige Park and some of the newer streetscapes around there.

I know you've been to the Annex as seen from one of your photo threads but I don't think I saw any Yorkville scenes. That's worth a look along with nearby U of T and area (the quads are fun to explore: Hart House, University College, Massey College, Trinity College), Philosopher's Walk, Royal Conservatory of Music building, Robarts, Queen's Park, Toronto Reference Library.

Then I'd recommend a walk through one of the ravines. My favourite is Moore Park Ravine around St Clair Ave E and it connects to the Brick Works. Cedarvale Ravine is also nice just off of St Clair Ave W and there is a popular one in the Beaches too called Glen Stewart Ravine but I haven't walked through there.

Last edited by shappy; May 5, 2026 at 6:42 AM.
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Old Posted May 5, 2026, 11:58 AM
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For Toronto, If you're up for a big walk, I'd recommend trekking down Queen West. You can basically walk from University to Roncy for 5km with small-scale streetfront retail the entire way. Few cities in North America have such a long contiguous commercial corridor. There's an endless number of restaurants along the way, and you can stop at Trinity Bellwoods and even do a detour up Ossington near the halfway point. If you want to change it up a bit, I would actually start on King Street at University, and then move up to Queen at Spadina. This way you get the entertainment district and all of the theatres, and you're not really missing much on Queen for the first km.

If you want to see something in the 905, you could do Downtown Oakville instead of Mississauga. It's quiet and quaint but has a good number of historic buildings along Lakeshore and the waterfront. I'd say it's the most interesting to see out of the old lakefront towns.
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Old Posted May 5, 2026, 3:59 PM
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The whole area with no freeways between Kitchener and Port Elgin is very enigmatic to me. I know nothing about this region and it seems like hundreds of km of flat farmlands. Is there something to see & do over there? I’m open to your suggestions!
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Old Posted May 5, 2026, 4:58 PM
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^Elora Gorge is worth a side trip, and so are some of the beaches along Lake Huron (Sauble Beach, Kincardine, etc....although the largest nuclear power plant in the world is nearby Kincardine).
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Old Posted May 5, 2026, 5:02 PM
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Elora, one of my favourite towns in Southern Ontario is located in that area. Cute town with interesting public spaces, the mill and the gorge. Adjacent town of Fergus is also quite nice. St. Jacob's Farmer's Market is very popular in the summer. But all these places are quite close to Kitchener, I'm not familiar with too much further north from there so not sure if that's of any help...
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Old Posted May 5, 2026, 6:04 PM
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Good suggestions Urbanite and Shappy - I've been to some of those places mentioned but not all. Even the ones mentioned are worth a revisit of course. Here's my Toronto photo album from the past two visits. I was in Yorkville but for some reason wasn't happy with the photos for the most part, I think the lighting was off or I was missing the photogenic scenes, or maybe it's not as dramatic visually as other parts of Toronto. I did get The Rock, lol. I'm staying right across the museum vs down at the Novotel on The Esplanade last year, so more central to that part of the city and an improved right out of door walking start, similar to when I stayed at The Annex on Bloor.

I'll add some ravines in and will 100% follow this plan, sounds like it's right up my alley: "For the Beaches, I'd recommend getting off the streetcar around Woodbine and walking east through the neighbourhood to the RC Harris building which is a fantastic location for architecture/photography. Kew Gardens is along the way (check out the dawn redwood trees) and will lead down to the boardwalk/beach. Some turn-of-the-century residential around there as well."

I've done portions of Queen West and been to Ossington, but having it as a dedicated walk sounds like the way to go. Oakville sounds interesting, so for a day trip that puts it up against Hamilton. If I was visiting for two weeks more side trips would be feasible but with only a week the time flies. Thanks for the insights, and hopefully next year I can get FrAnKs Quebec insights. I have family that wants to do the Quebec trip together, which means waiting for them to coordinate schedules and I don't want to add it on as a side trip from Montreal as I prefer staying in one location per trip.
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Old Posted May 5, 2026, 6:10 PM
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Elora, one of my favourite towns in Southern Ontario is located in that area. Cute town with interesting public spaces, the mill and the gorge. Adjacent town of Fergus is also quite nice. St. Jacob's Farmer's Market is very popular in the summer. But all these places are quite close to Kitchener, I'm not familiar with too much further north from there so not sure if that's of any help...
Elora looks great - thought this was funny, the man working out of that tiny box at the gatehouse of the hotel.

BC has countless spectacular natural location towns, and some really nice quaint historic towns, but for the most part it's far less refined ramshackle 20th century resource towns. Southern Ontario and Quebec seem to have a plethora of historic lakeside/riverside towns.
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Old Posted May 5, 2026, 7:04 PM
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Elora shouldn't be too busy in May, but if you can avoid weekends you will have a much more pleasant experience.

If you want a chill day away from the hustle of the city, the Island is the place to go. I never get tired of visiting it. And if you go on foot (not bike) stick to the Eastern end (Wards Island, Algonquin Island,) and you will love walking around the pedestrian only streets with cottage like homes. You almost forget you're in a big city.

Pro tip: If it's a nice day and the Ferry Terminal is busy just hop on a water taxi, they don't cost much more and you won't have to wait. You can take the ferry back for free. Pack snacks or lunch, the options are limited over there other then the Riviera Cafe, and Rum Shack.

Ward's Island by A Great Capture, on Flickr

If you go to the Beaches take the 501 Streetcar all the way to the eastern end and get off and chack out the R.C. Harris Water Treatment Plant if you like Art Deco buildings. You can't go in (unless it's Doors_Open)but it's a great place to start you walk back from.
R. C. Harris Water Treatment Plant by Jack Tome, on Flickr

Cabbagetown is often looked over and IMO it's one of the nicest downtown neighbourhoods to stroll through. It claims to have the largest continuous area of preserved Victorian housing in all of North America. It's home to the Riverdale Farm, The Toronto Necropolis full of historical figures who helped build this country. It's also has a cute little shopping area at Parliament and Carlton. Best place to eat here is The House on Parliament. Possibly the best English pub fare in Toronto. It's also very easy to get to on foot or transit if you are downtown.
12. The Lamb House by Billy Wilson, on Flickr

If you have a car and you like Chinese food you need to get yourself up to Markham. Go to the Pacific Mall, or go up to HWY 7 and you will find a ton of Asian fare, my Dim Sum go to is Xiao Long Bao.
Pacific Mall (太古广场), Toronto by James Kang, on Flickr

Also while up there you are about a 5 min drive to Unionville Mainstreet.
It's probably the nicest Main Street of any suburban Toronto in the GTA.
Unionville by Yong Loves Phone Photography, on Flickr

One last thing. If you are lucky enough to be in Toronto May 23 & 24, it's the annual Doors Open Event. https://www.toronto.ca/explore-enjoy/festivals-events/doors-open-toronto/
St. Lawrence Hall II by Jack Landau, on Flickr
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Old Posted May 5, 2026, 8:15 PM
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Elora looks great - thought this was funny, the man working out of that tiny box at the gatehouse of the hotel.

BC has countless spectacular natural location towns, and some really nice quaint historic towns, but for the most part it's far less refined ramshackle 20th century resource towns. Southern Ontario and Quebec seem to have a plethora of historic lakeside/riverside towns.
Elora also has a big cultural festival, but that's in the month of July.

Some of the towns between K-W and Kincardine are nice enough, but none strike me as tourist destinations. Arthur, Mount Forest, Palmerston, Walkerton, etc, etc always seem quite similar to me - a glimpse of late 19th/early 20th century Ontario but mainly service centres for the surrounding farming region. Cultural events (Elora, Drayton, Blyth) seem to happen mostly in the summer.
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Old Posted May 5, 2026, 8:56 PM
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Mostly agree. Ive had family in Kincardine since I was born and have done the drive from the GTA to the "west coast" countless times. Listowel, Wingham, Lucknow, Hanover, etc. Are not really distinct from each other. Walkerton is imo the most interesting but would wouldnt really recommend going out of the way to see it. My favourites are the ones on the water. Kincardine, Port Elgin, Southampton, Wiarton, Tobermory, Meaford, are all great little towns. Lots of good memories spending summers out there as a kid.
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Old Posted May 5, 2026, 10:26 PM
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^ Merci guys, it’s really appreciated.
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Old Posted May 5, 2026, 10:30 PM
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Thanks for the insights, and hopefully next year I can get FrAnKs Quebec insights. I have family that wants to do the Quebec trip together, which means waiting for them to coordinate schedules and I don't want to add it on as a side trip from Montreal as I prefer staying in one location per trip.
Ask me anything!
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Old Posted May 6, 2026, 2:21 AM
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Multiple cities can be discussed at once - so I'll start off with Toronto.

Heading there again for the third May in a row (hope to go to Montreal for the 2nd September in a row later this year) and looking for recommendations on places to explore that I might have overlooked. I've explored most of the downtown by foot, but I'll look to add the Beaches neighbourhood which I haven't been to yet, and like I did the first year I'll do the CN Tower, cause, come on, being on SSP who doesn't like a great view of an ever changing skyline. I've checked out the concert scene, and as with last year there really isn't much going on, which is a disappointment, so I might drop into a random live music club and hope for the best.

Also looking for good lunch/small plates type places - I've found social media is not your friend in this regard. Any photography, architecture or art exhibits worth checking out?

I haven't been to Mississauga - is there a compelling reason to visit beyond the Marilyn towers?
Some things to explore if you're an urbanist who's already been to Toronto before and crossed off all the downtown bucket list items:

- The Wychwood park neighbourhood and the Wychwood barns, which is lively on Saturday mornings when there's a farmer's market (nearest subway: St. Clair West)
- Shappy already mentioned Cabbagetown, the Riverdale park (cross to the other side to see the views from Broadview), and the Toronto Necropolis cemetery
- If you're not "cemeteried out", take the subway to Davisville, rent a bike share bike, then bike through Mount Pleasant cemetery, down through the Moore Park ravine to the Toronto Brickworks. It's all downhill this way.
- I assume you've been to the Ossington strip. The neighbourhoods to the west, Little Portugal and Brockton, are less well known, and more relaxed, but have a similar vibe
- If you're here May 23/24, Doors Open will be on, so that can probably scratch your architectural itch. Some of the venues might have long lines, like the RC Harris filtration plant. My favourite, in terms of easy access and interesting historical architecture, is the Don Jail or maybe Osgoode Hall and old City Hall
- I'm not a huge fan of the Beaches as a neighbourhood, but if you're going, then you absolutely should visit the RC Harris plant from the outside, and the nicest way to get to the Beaches is to walk south from Kingston road, through the Glen Stewart ravine, continuing through the Ivan Forrest gardens, then head west on Queen to Kew Gardens, go through Kew Gardens than east along the Boardwalk to the end
- Don't bother going to Mississauga City Centre, which is hard to get to, very spread out and hostile to pedestrians, and the condo towers which look impressive from afar, fall apart completely at street level up close. If you want to go to a suburban highrise cluster that actually offers something, my vote is North York Centre, which is packed with Asian hole in the wall restaurants (especially south of Finch on the east side), and is much easier to get to on the subway.
- I haven't been, but for less than half the price of a ticket to the CN tower, you can probably enjoy a cocktail at Aera, the bar on top of the main office tower of the Well. Obviously overpriced, and maybe not even a good cocktail, but you're paying for the view. I would probably save that for an odd time when everyone's at work like 4pm on a Tuesday so that you can get a table with a view.
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Old Posted May 6, 2026, 2:49 AM
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Heading there again for the third May in a row (hope to go to Montreal for the 2nd September in a row later this year) and looking for recommendations on places to explore that I might have overlooked. I've explored most of the downtown by foot, but I'll look to add the Beaches neighbourhood which I haven't been to yet, and like I did the first year I'll do the CN Tower, cause, come on, being on SSP who doesn't like a great view of an ever changing skyline. I've checked out the concert scene, and as with last year there really isn't much going on, which is a disappointment, so I might drop into a random live music club and hope for the best.

Not sure to what extent you might already be familiar with them, but I think you'd enjoy some of these areas (just based on some of your other photo subjects):

Parkdale: formerly upscale Victorian lakeside suburb turned post-war high-rise ghetto turned trendy hood. Has some great old Victorian mansions mixed in with mid-century towers in a messy but quintessentially Toronto way. One of the city's most vibrant and diverse neighbourhoods, anchored by the solid Queen St. retail strip.

Little Portugal: the vibrant Dundas strip slices diagonally through the tight-knit residential neighbourhoods of Seaton Village (the posher part) & Brockton Village (the more working class part). The web of narrow back streets, old homes, and corner retail is fun to explore.

The Junction: being an old railroad town that was later absorbed into the city makes it feel a bit like it's own little town. Meanwhile the neighbouring Junction Triangle has an interesting industrial mix; and which is (IMO) adjacent to the best parts of Bloor St. (Bloordale & Bloorcourt)

Rosedale & Summerhill: being the historic centre of wealth in Toronto, it's got a collection of Victorian mansions at their full splendour.



As Drew mentioned, there's also the annual Doors Open festival on the 23rd & 24th, which provides free access to all sorts of historically & architecturally interesting buildings - including some great viewpoints that aren't normally open to the public.
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Old Posted May 6, 2026, 3:56 AM
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- I haven't been, but for less than half the price of a ticket to the CN tower, you can probably enjoy a cocktail at Aera, the bar on top of the main office tower of the Well. Obviously overpriced, and maybe not even a good cocktail, but you're paying for the view. I would probably save that for an odd time when everyone's at work like 4pm on a Tuesday so that you can get a table with a view.

On the topic of rooftop bars & restaurants with skyline views: the Writer's Room at the Park Hyatt is another good one - unobstructed views over the ROM & UofT, and it's actually a decent bar.




I also like Evangeline at the Ace Hotel, but it's only a so-so view. The Broadview Hotel's rooftop isn't bad either. There's a new restaurant at the Manulife Tower rooftop as well: Mar'aa. No idea if it's any good (the earlier bars/restaurants up there certainly weren't), but it's one of the best views in the city.
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Old Posted May 6, 2026, 1:04 PM
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Echoing the above I'd suggest a walk down Queen West all the way through Parkdale, up Roncesvalles then loop back down Dundas W. Lots of places to grab a quick bite including both takeout and sit-down options. I'm currently obsessed with the sandwiches from Tutto Panino on Sorauren which parallels Roncy.

Can also take a side trip up the West Toronto Rail Path into the Junction Triangle - the stretch of Dupont between Osler and Lansdowne has started to get some interesting stuff and is bounded on the South by Bloor which is also worth a walk from that end into more central areas.

If you're going to the Beaches (also don't love the area but it is a beautiful walk in the summer) would also highly recommend the Riverside stretch of Queen E. One of the more "complete" looking streetscapes in Old Toronto IMO - buried hydro, good mix of old buildings and tasteful new infill, and usually puts a lot of effort into the look of the CafeTO streetside patio program. Can also go to the rooftop of the Broadview Hotel for great skyline views.

East Chinatown in the general area is a place lots haven't walked through and if you follow Gerrard St East to Jones there's a strip of cool restaurants/bars and then (a fair bit) further down is Little India which has both traditional and newer stuff - would highly recommend Lake Inez and Belle Isle for small plates. And Godspeed Brewery for some of the best traditional styles you can find on this side of the world.


The more I write the more I'm wanting to explore these areas as I feel like I've been trapped in my corner of the West End this horrible winter!
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