Looking northeast towards the Royal Oak Inn located at 376 Dundas St E and Ontario St in Toronto’s Cabbagetown South neighbourhood.
The building dates back to approximately 1876, when it was first listed in the Toronto City Directory as the Derby Arms. Over the years, the hotel has been known by several names, including Wilton House, Royal Oak Hotel, Royal Oak House, and Soupy’s/Stoopy’s Tavern. In the 1980s and 1990s, its dive-bar atmosphere attracted filmmakers; it appeared in movies like Cocktail, A History of Violence, and The Fly.
In 2013, the hotel underwent renovations, during which its exterior was covered with beige stucco. This change hid many of the building’s architectural details, including keystones and hood moulds above the first-floor windows and doors, as well as its brick and dormer ornamentation. The 25-room budget-friendly hotel was renamed the Royal Oak Inn. Last year, the exterior was repainted a dark grey with orange trim, as shown in the 2025 photo.
Then and Now
SOURCE
- City of Toronto Heritage Register: 376 Dundas St E
- Biographical Dictionary of Architects in Canada
- Toronto Star Newspaper Archives: Jul 29, 1983, pg C21
- The Globe and Mail Newspaper Archives: Nov 22, 2008, pg R9
- IMDb: Filming Locations – Stoopy’s Tavern
- Photo: Denise Marie for TorontoJourney416
- City of Toronto: Maps
- Toronto City Directory courtesy of Toronto Public Library
