Union Station to the Financial District
You exit Union Station onto Front Street and the glass towers start immediately. This is the part of Toronto that photographs well, the part with the hedge funds and the corporate law firms where everyone walks fast between buildings connected by underground tunnels. When snow falls those tunnels matter. When heat arrives they are optional but still appreciated.
The PATH system runs for thirty kilometers under these towers. You can walk from Union to the Eaton Centre without seeing daylight, past food courts that serve the office workers and banks that never seem to have customers. The PATH has its own geography. People who work here know which exit delivers them closest to their desk. You will get lost the first three times.
Above ground, King Street holds the restaurants where expense accounts get used. Canoe on the 54th floor of the TD Tower does Canadian ingredients at $48 for a main. The view includes Lake Ontario and the Islands. Two blocks north, the old bank buildings from the 1920s sit between the newer towers, their limestone facades kept clean. Toronto preserved some things. Not many, but some.
The Financial District empties after 6pm on weekdays. On weekends it is a movie set without actors. This is not where anyone lives by choice.
Crossing into the Entertainment District
Walk west on King and the towers thin out past Simcoe Street. You are now in what gets called the Entertainment District, though that name is aspirational. The Princess of Wales Theatre and the Royal Alexandra face each other across King. Between them, restaurants charge $22 for a cocktail before curtain time.
This neighborhood exists in two-hour bursts around showtimes. The pre-theatre crowd fills the patios at 5:30pm, then disappears into the venues. By 11pm the same patios hold a different group, younger and louder, spilling out of the clubs on Adelaide. The staff at Kit Kat and Lavelle change the music and the lighting and serve the same space to two audiences who would not recognize each other.
John Street runs north through this area toward the Art Gallery of Ontario. The AGO sits in a Frank Gehry renovation that locals either love or find excessive. Inside, the Group of Seven paintings take up multiple rooms. Tom Thomson's "The Jack Pine" is smaller than you expect and always has people standing in front of it. Admission costs $25 ($18.50 USD) but Wednesday evenings after 6pm are free and crowded.
Kensington Market to Chinatown
West of Spadina Avenue the grid breaks down and Kensington Market starts without announcement. This is the neighborhood that travel writers call bohemian, which means the buildings are old and the rents are rising but have not yet won. Vintage clothing stores operate out of houses painted purple and turquoise. The cheese shop on Augusta has been there since the 1950s when this was a Jewish neighborhood, then Portuguese, now a mix that has not finished mixing.
Saturday mornings the market is full. Tourists take photos of the murals. Locals buy produce from stands that put prices on cardboard signs, CAD $3 for a pound of tomatoes that taste better than the grocery store versions. The jerk chicken place on Augusta has a line. So does Rasta Pasta. Neither takes cards.
One block east, Chinatown absorbs Spadina Avenue for ten blocks. The signs switch to Cantonese and Vietnamese. Rol San does dim sum where you point at carts, $4.80 ($3.55 USD) for har gow that arrive steaming. Across the street, herbalist shops sell dried ingredients you will not recognize. The prices are not posted. You ask or you do not buy.
The people in Kensington do not shop in Chinatown. The people in Chinatown do not browse the vintage stores. These neighborhoods share a border and not much else.
Queen West and the Art School Effect
Queen Street West between University and Bathurst used to be where the art students opened galleries they could afford. Some of those galleries are now sneaker stores and matcha cafes where everything costs $8. The students moved west or gave up. What remains is a street that tries to look like it did in 2005.
OCAD University sits at the corner of McCaul, a building on stilts painted in a checkerboard that makes architects argue. The students still come here but they live somewhere cheaper, probably east of the Don Valley or north of Bloor where the subway still reaches.
Trinity Bellwoods Park holds the picnic crowds on summer weekends. Someone is always playing music badly. Someone else is always selling popsicles from a cooler without a permit. The albino squirrels are real, a genetic quirk the park has maintained since the 1990s. People feed them. The city posts signs asking people not to feed them. The people keep feeding them.
Across the Viaduct to the Danforth
The Bloor Viaduct crosses the Don Valley and suddenly you are in Greektown, which is still Greek in the restaurant names if not the ownership. Mezes on Pape does saganaki tableside, the cheese flambéed with Metaxa for $14 ($10.35 USD). Christina's makes baklava that sells out by 3pm most days.
This is not downtown by anyone's measure except the people who live here. The rents are lower. The buildings are three stories, not thirty. You can park on the street after 6pm without an app. It feels like a different city because it is a different city, one that happens to share a subway line with the towers on Bay Street.
The people who work in the Financial District do not eat dinner on the Danforth. The people who shop in Kensington do not cross the viaduct for baklava. Toronto contains multiple cities, each complete with its own groceries and complaints and evening routines. They overlap on the subway. They do not overlap much else.
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