Looking northeast towards the Royal Oak Hotel, today the Royal Oak Inn, at the corner of Dundas St E and Ontario St, in the Cabbagetown South neighbourhood of Toronto.
The hotel was built in the mid-1870s in the Second Empire style and was originally called the Derby Arms, operated by Thomas Gibson. Over the years, it changed hands several times and was known by various names, including Wilton House, which it was called from the early 1900s until it was renamed the Royal Oak Hotel in 1915. The hotel retained the Royal Oak name until 1970, when it became the Royal Oak House.
In the 1980s, it was transformed into Soupy’s Tavern (also referred to as Stoopy’s Tavern). Known for its dive bar atmosphere, the hotel’s unique character has attracted filmmakers, leading to its appearances in movies such as Cocktail and A History of Violence.
In 2013, the hotel underwent renovations, and many of the building’s architectural details were covered with beige stucco. It was then renamed the Royal Oak Inn. In 2024, the hotel received a fresh new look, as shown in the recent photo.
Then and Now

SOURCE
- City of Toronto Heritage Register: 376 Dundas St E
- Biographical Dictionary of Architects in Canada
- City of Toronto Heritage Register: 376 Dundas St E
- 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
- Vintage Photo: City of Toronto Archives
- City of Toronto: Maps
- Toronto City Directory courtesy of Toronto Public Library
