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Sherbourne - St James Town - Cabbagetown - Regent Park - Underpass Park - Cork Town - Distillery

Richard Longley

Our journey through Toronto takes us from Sherbourne Street to Howard Street, where the Selby Hotel, Cooper Mansion, and Anson Jones House stand as examples of historic houses restored and repurposed, breathing new life into the cityscape. We then venture into St. James Town, inspired by Le Corbusier's vision of "Towers in the Park." Home to 17,000 residents across 19 towering buildings, it presents a complex narrative: a utopian dream for some, a dystopian reality for others, or perhaps a community that's simply misunderstood.

Next, we explore Cabbagetown, a neighbourhood meticulously preserved, boasting the quaint Riverdale Farm—a slice of rural tranquility in the urban expanse—and the Necropolis, a final resting place for notable Canadians. Our path leads us to Regent Park, an emblem of ongoing urban renewal efforts aimed at fostering better lives.

Underpass Park emerges as an unexpected delight, transforming the space beneath a Don Valley Parkway offramp into an urban playground and art gallery, showcasing the city's innovative spirit. In Corktown, the eye-catching cube houses and the rugged architecture of the Dominion Foundries mark a juxtaposition of modernism and industrial heritage, where once, the work of William Davies earned Toronto the nickname "Hog Town."

The journey concludes in the Distillery District, once the heart of the Gooderham’s whisky production, now pulsating with the energy of the Soulpepper Theatre, Balzac's Coffee, and an array of galleries and restaurants. It's a perfect spot to unwind and reflect on Toronto's enduring capacity for transformation—a city that continues to evolve, layer by layer, into a tapestry rich with history, culture, and innovation.

Walk Start:

Sherbourne subway, SE corner Sherbourne at Bloor.

Distillery District, close to 504 King streetcar 65 Parliament bus. Parliament Dropouts close to TTC available at Gerrard, Dundas, Queen, King, Parliament Streets.

Walk End:

Date: May 5

10:00 a.m. - 12:30 p.m.




Advocacy and Politics
Architecture and Urban Planning
History and Places
People and Communities


Breaks encouraged, Dog-friendly walk, Walk leader will use audio amplification, Dress for weather of the day. Bring water. Washroom at Riverdale Farm, break prior to the walk recommended.

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