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100

This Toronto streetcar system, still running today, celebrated its 100th anniversary in 2011.

What is the TTC

100

This Toronto theatre is actually two stacked theatres, one on top of the other, famous for its beautiful “garden” ceiling.

What is the Elgin and Winter Garden Theatre?

100

Founded in 1670, this Toronto flagship store became famous for its striped wool blankets, in addition to its Christmas windows and seasonal traditions.

What is the Bay

100

This Toronto neighborhood is famous for its streetcar-lined avenues, Victorian houses, and the annual Pride Parade.

What is Church-Wellesley Village?

100

This Toronto craft brewery is located in the historic Roundhouse building and is known for its green-bottled pilsner beer.

What is Steam Whistle

200

This once-iconic Toronto airport, located near the waterfront, closed in 1939 when operations moved to Malton (now Pearson).

What is Toronto City Airport / Island Airport

200

In the 1980s, this Toronto club became the center of the punk and new wave music scene.

What is The Horseshoe Tavern?

200

Founded in 1954 on Toronto’s Bloor Street, this store helped define Canadian men’s fashion by popularizing tailored suits and attracting both everyday professionals and high-profile clients.

What is Harry Rosen

200

This Toronto district, once a separate municipality before amalgamation in 1998, is known for its dramatic Bluffs, the Toronto Zoo, and a mix of diverse residential communities.

What is Scarborough?

200

This Toronto-based peanut butter brand became popular in the 20th century for creamy and crunchy varieties.

What is Skippy

300

Built in 1929, this bridge spans Toronto’s Don Valley and was celebrated for its engineering design at the time.

What is the Prince Edward Viaduct / Bloor Viaduct?

300

Opened in 1963, this Toronto venue was the first purpose-built concert hall in Canada, now home to the Toronto Symphony Orchestra.

What is Roy Thomson Hal

300

This Toronto-based company, founded in 1957, started by making wooled vests and raincoats but became globally famous for its luxury parkas worn in the Arctic and on fashion runways.

What is Canada Goose

300

Located in North Toronto, this neighborhood is known for its Edwardian and Victorian homes, tree-lined streets, and community clubs, often called “Toronto’s Garden District.”

What is Rosedale?

300

During World War I, this Canadian sugar company played a key role in supplying sugar for troops and domestic use.

What is Red Path Sugar

400

Before cars became common, this Toronto service provided horse-drawn carriages for hire throughout the city in the 19th century.

What is a hackney carriage / cab

400

This Toronto theatre opened in 1920 and was originally designed to host vaudeville shows and silent films.

What is the Pantages Theatre

400

Before online shopping, many Torontonians browsed thick seasonal catalogs from this department store, which once anchored Queen Street West.

What is Eaton's

400

Question: This Etobicoke neighbourhood is known for its storybook-style homes, pedestrian-friendly “village” shopping streets, and proximity to the Humber River trails, giving it a quaint, old-world charm within Toronto.  

What is The Kingsway?

400

Founded in Toronto, this brand is famous for baking mixes and bread products across Ontario.

What is Robin Hood Flour

500

This Toronto-based airline, founded in 1937, later became part of Air Canada.

What is Trans-Canada Air Lines (TCA)?

500

This downtown Toronto venue combined Italian cuisine with nightly live jazz, creating a unique cultural experience for diners.

What is George’s Spaghetti House?

500

Founded in 1879 in Toronto, this boutique became famous for luxury jewelry, watches, and engagement rings, and remains a Canadian icon today.

What is Birks

500

This North York neighbourhood, nestled along the Don River Valley, is known for its affluent homes, winding streets, and a tragic 1960s subway construction accident that made headlines across Toronto.

What is Hogs Hollow

500

This Toronto bakery became famous for Jewish rye bread and bagels, distinct from Fairmount or Streit’s.

What is Kleinburg Bakery / Koffler’s

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