In early 18th century, Osterhout Log Cabin was built in Guildwood. The log cabin is one of Toronto's oldest buildings still standing. . In 1914, the Guild Inn was opened. Initially a private residence, it later became an art colony, and a hotel. From 1941 to 1947, the inn was leased by the Government of Canada as a base for the Women's Royal Naval Service, HMCS Bytown II, and later a military hospital. After Metropolitan Toronto was formed in 1954, taxes on the Guild Inn property increased to the point that the owners Rosa and Spencer Clark decided to sell of their property, which became the basis for the Guildwood Village subdivision. The Clarks remained involved with the development of the subdivision, in its design and layout to preserve as many trees in the area as possible. Development started in 1957 with the famous "Avenue of Homes" display of upscale homes. The community introduced a number of new ideas in subdivision design, including winding roads and cul-de-sacs to reduce through traffic, and underground power and phone lines. "Rear-lot parks were modelled after English footpaths as walkways within the community." The Clarks helped design the entrance gates to the subdivision. After most of Toronto's Stanley Barracks was demolished in 1953, its gates were salvaged and re-erected at the entrance to Guildwood Village. These gates, now called the "Guildwood Gates" still provide a unique and grand entrance to the community at the corner of Kingston Road and Guildwood Parkway. Guild Park is famous for its historical architectural fragments from the façades of demolished buildings in Downtown Toronto. Just west of the Guild Inn is Sir Wilfrid Laurier Collegiate Institute.
Guildwood Village Flag
The Guildwood Village Flag was designed by Marsha Leverock Westergaard and was adopted by the Guildwood Village Community Association on June 12, 2018. The Guildwood Village flag can be seen flying in Guildwood Village from cars, store windows and residential flag poles. The flag has deep meaning in its symbols and colours. The four quadrants read Guild – Wood – Village – on the Bluffs and represent Guildwood Village’s rich history of arts and culture, the abundant woods and green spaces, unique mid-century architecture, the Scarborough bluffs and a strong, vibrant Guildwood Village community.
Guildwood is home to several municipal parks, all of which are managed by Toronto Parks, Forestry and Recreation Division. Many of these parks are situated near the Scarborough Bluffs and the Toronto waterfront. Parks in Guildwood include Elizabeth Simcoe Park, Grey Abbey Park, Guild Park and Gardens, South Marine Park, and Sylvan Park. Guild Park and Gardens is notable for its collection of relics, collected from the remains of demolished buildings primarily from Downtown Toronto.
Guildwood Parkway is the main roadway in Guildwood. The eastern end of the roadway splits north, and east, with the northern portion forming Morningside Avenue. Many of the streets in the Guildwood development were named by Rosa and Spencer Clark.
Bethune - after Dr. Norman Bethune
Bledlow - after the England home of Spencer Clark's grandmother
Bournville - after the Cadbury's Chocolate model town in England
Cadbury Court - after the Cadbury family
Catalina - after the island off the coast of California
Earswick - after the Rowntree Chocolate model town in Yorkshire, England
Livingston Road - after the owner of the property who was treasurer of the T. Eaton Company
Nuffield - after Lord Nuffield, founder of Morris Automobiles in Britain
Rowatson - after Robert Watson McClain, owner of the farm the street is sited upon
Sir Raymond - who planned a model town in Manchester, England
Sonneck Circle, Sonneck Square - an old castle in Germany
Toynbee Trail - after Arnold Toynbee, British Historian, Professor and Author
Westlake Road - after the brothers who were developers of the property.
Source: Lidgold
In popular culture
The Guild Park and Gardens is home to many movies such as The Skulls, and the neighbourhood is used by TV shows such as Odyssey 5. Drake's video "Headlines" was partly filmed at Guild Park by the amphitheatre. Saini Surinder's music video for a currently unreleased track as of February 2012 was shot at the Guildwood amphitheatre with Director Jared Pelletier.