Bay-Cloverhill

Windsor Arms Hotel
18 St Thomas Street
This heritage-designated hotel dates back to 1927, when it was originally designed by architect William Arthur Price as a four-storey building that blended in with the many Victorian-era University of Toronto buildings nearby. In 1976, the hotel was the site of the very first Toronto International Film Festival (TIFF), which was originally called the Festival of Festivals. The founders of the festival - Bill Marshall, Dusty Cohle, and Henk van der Kolk - intended to bring the best films from other festivals around the world to Toronto, and to create a warm, welcoming atmosphere that would attract major Hollywood productions. TIFF has since become one of the largest film festivals in the world, and the Windsor Arms Hotel continues to be a key location associated with the festival. The hotel underwent a major renovation in the 1990s, which saw the original structure torn down and then recreated with a 19-storey residential condominium added on top.

The Colonnade
131 Bloor Street West
This landmark heritage-designated building was constructed in the early 1960s, designed by architects Gerald Robinson and Tampold and Wells in Brutalist style. It is one of the first buildings combining residential and commercial uses in the city and in Canada, which was considered to be revolutionary at the time. It is considered to be a physical manifestation of the transformation the Yorkville area was undergoing at the time from a counter-cultural village to a bustling, sophisticated urban neighbourhood. A plaque one the on and a half turn spiral staircase leading up from the courtyard at the front of the building notes that it is the only one ever built without a central support.

Gardiner Museum
111 Queen's Park
The Gardiner Museum was first established by philanthropists George and Helen Gardiner in 1984. Together they accumulated a large collection of ceramics and decided to build the museum in order to share it with the public. Following the passing of her husband in 1997, Helen (who passed in 2008) took on the role of chair of the museum's capital campaign and pushed for the expansion and renovation of the building. The campaign raised $17 million, and the museum was closed in 2004 until 2006 once they were completed. The renovations saw a third floor expansion on top of the original structure as well as an expansion to the basement, which made room for educational studios and research activities. The sculpture at the front of the building is by acclaimed Toronto-based ceramist Shary Boyle and is called 'Cracked Wheat'. Today, the Gardiner is the only museum dedicated to ceramics in Canada and features approximately four thousand pieces.

Annesley Hall
150 Charles Street West
This heritage-designated building is the first purpose-built all female residence at a Canadian university. It was designed by architect George Martel Miller - who also designed other famous buildings in Toronto such as Massey Hall and Gladstone House - in Queen Anne Revival style and officially opened on October 1, 1903. It was named in honour of Susannah Annesley, the mother of founder of Methodism John Wesley, and was financed largely thanks to a financial gift by the estate of Hart Massey, a businessman who built the agricultural equipment firm Massey Ferguson. It has since been designated as a National Historic Site of Canada by the Government of Canada due to its architectural features and its significance marking the achievement of women's access to higher education.

Marshall McLuhan Way & Elmsley Place
Along St Joseph Street between Queen's Park Crescent East and Bay Street
Many noteworthy sites can be found along or nearby this street, which is part of the University of Toronto campus (specifically University of St. Michael's College). The street is named after Marshall McLuhan, who was a professor at St. Michael's College and went on to become Toronto's most famous intellectual thanks to his ground-breaking theories on the effects of mass media on human consciousness. McLuhan's first home in Toronto was also located along here, at 91 St Joseph Street, in a building that has since been torn down. A plaque commemorating McLuhan and his intellectual significance can be found near the intersection of St Joseph Street and Elmsley Place, a small private street that features a cluster of picturesque formerly residential homes (some dating back to 1892) and was one of Toronto's first subdivisions.

Myfanwy MacLeod 'Promise'
Northwest Corner of Bay Street and St. Joseph Street
'Primrose' is based, in part, on the story of a baby donkey who was born prematurely. Thanks to vets who fitted her with a pair of pink casts, Primrose was able to walk. This story embodies the phenomenon of heart-warming and inspirational news reports about animals. But the little donkey is more than just a way to end the news day on an upbeat note, she is also a creature deeply embedded in myth and folklore. In the West, the donkey has often been used to symbolically represent notions of service, suffering, humility, and peace. Primrose is part of a trilogy of monumental animal sculptures by MacLeod, along with 'The Birds' (2010), and 'The Lady' (2017), which draws on the symbolic language of animals in Western Christian art and literature.

Dora de Pedery-Hunt 'George Faludy Place'
Across from 25 St. Mary Street
'George Faludy Place' is located across the street from 25 St. Mary's St. where Mr. Faludy, one of Hungary's greatest poets, lived for much of his 22 years of self-imposed exile from Hungary. 'George Faludy Place' is an initiative of the Toronto Legacy Project, which honors notable artists, scientists and thinkers who have enriched the life of Toronto, by embedding their names in the fabric of the city. Dora de Pedery-Hunt is perhaps best known for moulding the image of Queen Elizabeth II seen on Canadian coins.

Former Club Manatee
11 St. Joseph Street
This heritage-designated building was constructed in the 1890s for a company called Rawlinson Cartage, one of the first express and storage firms in the City of Toronto. In the 1970s, it was home to Club Manatee, an important space for the LGBTQ2S+ community. Parts of the 1977 Canadian film 'Outrageous!' were filmed here, which centred on the relationship between a gay drag performer and his schizophrenic best friend, and was the first queer film to have a wide North American theatrical release. Craig Russell, who starred in the film as drag performer Robin Turner, was known to frequent the Club Manatee stage when it hosted its drag shows as featured in the film. The building has since been renovated to become part of a condominum development.

Yonge Street Heritage Conservation District
Along Yonge Street between College Street and Bloor Street
This stretch of Yonge Street was heritage designated in 2016 in an effort to preserve the many historic two-to-three storey buildings along the strip. Some of the more notable buildings located in this district include the former site of the St. Charles Tavern at 484-488 Yonge Street. Easily identifiable thanks to its clock tower, the tavern opened in 1951, and became one of the most prominent gay bars in Toronto by the early 1960s. It was legendary for its Halloween drag promenades, which attracted thousands of onlookers. The site is currently being redeveloped, but its famous clock tower will be maintained. Other notable buildings included in the district are a series of rowhouses between 45 and 63 St Nicholas Street (these are private property and should be observed from the street). These rowhouses were constructed in the 1880s and all feature their own unique name, and constitute one of the few remaining examples of 10 contiguous rowhouses with well-preserved original details that can be found in downtown Toronto.

Women's College Hospital & Dr. Emily Stowe
76 Grenville Street
Prior to her arrival to Toronto in 1867, Dr. Emily Stowe studied medicine in New York City. At the time, the University of Toronto was not accepting women to any of their faculties, including medicine. In response, Dr. Emily Stowe and several other like-minded people, founded Woman's Medical College at 289 Sumach Street in 1883. In 1898 a clinic called The Dispensary was opened at the College. The clinic enabled female patients to receive unique services from women doctors. The college operated until 1905 when the University of Toronto finally began admitting female students to the medical school. From there, a group of Toronto women began to establish what was to become the Women's College Hospital, which opened in 1913 at 18 Seaton Street. The hospital soon reached capacity, proving the need of a hospital for women, run by women. In 1935 the hospital moved to its current location.

Whitney Block
99 Wellesley Street West
This building was completed in 1925 in Art Deco style and named after Premier of Ontario James Whitney, who was in office from 1905 to 1914. It is the first government office building constructed by the Ontario government, as the Ontario Legislative Building across the street no longer had enough space to accommodate the growing number of civil servants. It hosted many unique uses, including provincial veterinary services on the 6th floor that required animals to be brought up via a hand-cranked elevator. The building has been mostly abandoned since the 1960s as it does not meet modern fire codes with only one main stairway and a poor ventilation system. It is currently undergoing extensive renovations to bring it up to modern standards so it can once again house provincial workers.

Queen's Park & Ontario Legislative Building
110 Wellesley Street West
This property was originally part of 168 acres of land purchased by Ontario's first university, King's College, in 1828/9. King's College later became the University of Toronto and, in 1859, decided to lease 49 acres of its land to the City of Toronto for 999 years to create a public park. In 1860, Queen's Park officially opened and became the first municipal park in British North America and was named in honour of Queen Victoria. The park was long considered for new parliament buildings and construction of the Ontario Legislative Building was completed in 1893, with expansions completed in 1912. The building (also known as the Pink Palace due to the pink sandstone used in its construction) was featured on the RUSH album cover for 'Moving Pictures'. Today the property still features a park behind the building that plays host to several events and features several monuments and statues dedicated to notable people and events in the province's history.

Ontario Fire Fighters Memorial
Northeast Corner of Queen's Park and College Street
This memorial - designed by the late sculptor Siggy Puchta - is dedicated to the hundreds of fire fighters who have died in the line of duty in Ontario. It was first dedicated in June 2005, and depicts a fire fighter rescuing a child from danger. The base of the memorial also features a Maltese Cross, which is an international symbol for firefighting. The first name listed on the memorial is that of William Thornton, who perished in the line of duty on November 24, 1848 at a fire near present-day King Street East and Church Street. At the time, most fire fighters were part of volunteer brigades, pulling manual pumpers by hand with water drawn from Lake Ontario. A annual ceremony is held at the memorial to honour those who have died in the past year.

Jacqueline Comrie 'March of the Suffragettes' Artbox
Northeast Corner of College Street and Elizabeth Street
'March of the Suffragettes' takes the College Street community back in time to Victorian Toronto.

Native Child and Family Centre
30 College Street
Native Child and Family Services (NCFST) was founded in 1986 by Elders, Knowledge Keepers, grassroots leaders, and community members. It provides multiple services including holistic, culture-based programs and services for Aboriginal children and family. The building provides a space that allows urban aboriginals to reconnect with nature in the heart of downtown Toronto. The bold sign at the entrance is in the shape of an Ojibwe hand drum and, once inside, the building exudes Indigenous culture through the natural materials used in the design, the art displayed and the serene green space on the roof. The four-storey building includes office space and a community hall that allows NCFST to provide clients with a variety of services including the Early Years Centre, Community Kitchen and Youth Program. The green roof is a unique space that is designed as a contemporary version of a longhouse with a healing lodge and fire circle, surrounded by a beautiful roof garden.