If Toronto has a midtown hub - a second heart of the city that acts as a nexus for transit, entertainment, residences, business, and retail - it is undeniably Yonge & Eglinton. Today, the area is a vibrant and affluent neighbourhood, offering the perfect bend of urban convenience and outdoor space, but how did it evolve from cattle fields to Castlefield? Let’s take a look back at the history of Yonge and Eglinton to see how the uptown downtown came to be.

Early 19th century
The neighbourhood is settled by Europeans who establish the farming village of Eglinton. The village becomes part of the largest cattle grazing region in Upper Canada. source

1874

In 1874, a Masonic Hall is built on the northwest corner of Yonge and Montgomery. The first floor is rented to the Township of York for Council meetings. In 1881, a new Town Hall is built on the site, and from 1909 to 1912, the area’s first high school is housed on the second floor. source

1885
On January 26, 1885 The Metropolitan Street Railway begins operating a horse-drawn streetcar route that runs along Yonge Street between the crosstown CPR rail line (near Summerhill Station) and Eglinton Avenue. Rapid housing development soon follows. source
 

1890
As the population grows, the area incorporates and becomes the town of North Toronto. source

1912
North Toronto is annexed to the city of Toronto. source

1913

Oulcott’s Hotel (the former site of Montgomery’s Tavern, famous for being the starting point of the 1837 Rebellion) is purchased by the government and refurbished for use as Postal Station K. Today, Postal Station K is home to Stock T.C., a gourmet grocer and neighbourhood hot spot. source
 

1920s to 1940s

Construction on new houses continues to accommodate the growing population. Architecture consists of Tudor and Craftsman bungalows, and semi-detached Victorian, Georgian and Colonial styles. source

1922

The Capitol Theatre opens on the northwest corner of Yonge and Castlefield. Built for Ronald McClelland, a native of Kingston, Jamaica, the theatre features vaudeville shows and silent films. What it doesn’t include is a candy bar, a concession to the neighbouring Laura Secord shop, just outside the entrance. A refreshment stand won’t be added until 1954. source and source

1932

Fire Station 134 (formerly TFD 28) is built at 16 Montgomery Avenue. The architecture is designed to match the surrounding homes, and today, remains largely unchanged. source

1933

Plans are submitted for a theatre on Yonge, near Manor Road. The simple, unadorned architecture by Kirk Hyslop reflects the overall feeling of the recent Great Depression. Originally named the Oriole Theatre, it is later renamed the somewhat redundant, Cinema Theatre, and eventually, the International Cinema. In 1947, Shakespeare’s “Henry V” plays for a record-breaking nineteen weeks. The theatre is decorated in the colours of the French flag to mark the occasion. source

1954
The Yonge subway line opens its first twelve stations. It is Canada’s first subway and runs 4.6 miles (7.4 kilometres) from Union to Eglinton. The project costs $50.5 million and uses 420 tons of cast iron pipe, 1.4 million bags of cement, 15 million b. feet of lumber, and 10,000 tons of structural steel. source

1961

The first set of plans is drawn up for the Yonge Subway northern extension. The plans are modified several times before being approved by the city in 1967 with new stations at Lawrence, York Mills, and Sheppard. Two years later, a decision is made to further extend the line to Finch. It will be another few years before the line is operational, with the first section opening in March 1973, and the second, one year later, in 1974. source

1960s/70s
The area continues to grow. New office buildings, condominiums, stores, and cinemas bring a large population influx. source

1974
Construction of the Yonge Eglinton Centre finishes. The complex includes a 23-storey rental apartment building at 411 Duplex Avenue, followed by 20 Eglinton West, an apartment building at 33 Orchardview, an office tower at 2300 Yonge Street, and an entire block of retail at the base. source

1980s

50s-inspired diner, Lime Rickey’s, becomes an iconic establishment on Eglinton. Patrons flock to the venue for classic plates, jukebox tunes, and deluxe desserts like “the kitchen sink” – a gargantuan ice cream sundae where 16 scoops of ice cream disappear under a thick layer of crushed up Kit Kat, Smarties, and other assorted candy bars. source  

1998
Metropolitan Toronto and the six municipalities amalgamate into the City of Toronto. Yonge & Eglinton becomes the new "midtown" of the city (a role previously held by Bloor Street). source

2006

Yonge and Eglinton is designated an "urban growth centre" by the provincial government, with the goal of creating a complete, inclusive, livable community with a variety of housing options, community services, building types, public spaces, shopping and economic opportunities, parks, and green spaces. People are already flocking to the neighbourhood, lured by the cheeky moniker, “Young & Eligible,” named for its large demographic of young, urban, stylish professionals. source

2008

Metro announces plans to consolidate the company’s variety of food brands under the Metro banner. This applies to all the Dominion stores in the Toronto area, including the one at the Yonge Eglinton Centre, which has been part of the site for more than three decades. Another long-time tenant? Tamblyn Drugs, one of the original businesses on the northwest corner. They will eventually be sold to Loblaws, then UK pharmacy chain Boots, and finally, Pharma Plus, which still has a location on site today. source

2014

The TTC celebrates the 60th anniversary of the Yonge subway line. Riders note the marked difference between the original cost of a token (10 cents) and the cost today ($2.70). source

2016

Work is complete on the massive renovation of Yonge Eglinton Centre. The project is an impressive example of urban renewal, revitalizing the public realm at the northwest corner with a 46,000-square-foot retail expansion, a 51,000-square-foot interior retail renovation, a 209,000-square-foot office tower expansion and renovation, a publicly accessible green rooftop patio, open year-round, and a 4-storey glass atrium that now functions as a neighbourhood mini-hub. source
 

2024
The new light rail line, Line 5 Eglinton, is scheduled to open, with 25 stops between Kennedy in the east and Mount Dennis in the west. The route will link to 54 bus routes, three TTC subway stations and GO lines. source