Cabbagetown-South St. James Town

St. James Cemetery
635 Parliament Street
St. James Cemetery is the oldest cemetery in the City of Toronto, in continual operation since 1844. The Anglican Church chose this large plot on the hill overlooking the ravine to be the cemetery as this location was originally several miles beyond most of the homes and shops in the city, and surrounded by farms. Architect John G. Howard was selected to design the layout of the grounds in 1842. The Chapel of St. James-The-Less was opened on the site in 1861, only 17 years after the opening of the cemetery. Designed by F.W. Cumberland, the Chapel has been a Toronto landmark ever since. The cemetery is the resting place of numerous prominent citizens and historical figures of Canada.

Wellesley Cottages
1 Wellesley Cottages
*Note: Private property. Please observe the houses from the laneway only. During the 1851 Great Exhibition (in London, England), visitors flocked to view the new Model Dwellings, houses designed with health, sanitation and design at the forefront. These brick buildings became the ideal template for Victorian workers, and were emulated in various parts of the world. In 1865, Canadian Farmer magazine published the plans for a Cheap Country Dwelling House. This home took inspiration from the model dwellings, and is exemplified by a peak with ornamentation over the door, symmetrical windows and graceful appearance. The homes along Wellesley Crescent are based on these plans, and turned into a row of ideal workers cottages that represented the pinnacle in health and sanitation for the residents within. Today, this stretch of identical homes gives a glimpse into the modern process of neighbourhood planning.

Overlooking Mouth of Castle Frank Brook
500 Wellesley Street East
This point, roughly where Bloor Street crosses the Don River, was a significant place of First Nations travel and sustenance. This point along the Don River is where the Davenport trail, perhaps the most prominent East-West First Nations trail in the Toronto area, crossed the Don River and turned South-Eastward towards what is now the Beaches neighborhood and then continuing Eastward along the Lake Ontario shoreline. Just west of this location, the Davenport trail was crossed by a North-South trail, one of the arms of the Toronto Carrying Place portage, that roughly followed the Don River watershed. These trails facilitated much First Nations and Métis movement through this area in the pre-colonial era, through the early fur trade, and into the nineteenth century. They also inspired the routes of their contemporary counterparts: Davenport Road and Yonge Street. In the Don River Valley at the point of the Davenport trail crossing, wild rice (minomeen, meaning the 'good seed' in Anishinaabemowin) used to grow. Minomeen has long been a very important and culturally meaningful part of Anishinaabe foodways and diets and its growth was encouraged throughout the Great Lakes watershed. These Minomeen beds also provided important habitat and food for ducks and other waterfowl, and so it is unsurprising that many migrating ducks frequented this area. When the Mississaugas were pushed out of their lands in Toronto and the subsequent increase in various forms of industrial development along the Don River, the minomeen fields disappeared. Anishinaabe people still plant and harvest minomeen today in other areas, but this practice is threatened by global corporations and settlers that dislike minomeen beds in the lake shallows by their cottages.

Toronto Necropolis
200 Winchester Street
Opened in 1850, the Toronto Necropolis is one of the oldest cemeteries in the city. A necropolis is typically characterized by elaborate tombs and monuments, and are usually found outside of city limits. While this would have been the case in the nineteenth century, the grounds of the Toronto Necropolis today are firmly within the city boundaries. The vast array of sculptures, Victorian buildings, stained glass windows and distinctive High Victorian Gothic architecture all contribute to the picturesque nature of the site. The Necropolis is the final resting place for several well-known luminaries, including City Alderman William Peyton Hubbard, New Democratic Party leader Jack Layton, Second World War nurse Kay Christie, and Dr. Anderson Ruffin Abbott, the first Black-Canadian surgeon.

Riverdale Farm
201 Winchester Street
The Riverdale Farm property was once owned by John Scadding, an early settler of the Town of York (now Toronto), who served as clerk to Upper Canada's first lieutenant governor, John Graves Simcoe. The City of Toronto purchased the land from Scadding in 1856. Riverdale Farm was built by the City as a tribute to Ontario's small, family farm heritage, and opened in 1978. The farm sits on the site of Toronto's first zoo, Riverdale Zoo, which closed in 1974. Visitors can still see some remnants of the old zoo, such as the zookeeper's residence, known as the Donnybook, and the Island House. Found just down the street from the farm is the Cabbagetown Farmers' Market, which offers local and sustainable food and production methods to the community.

Miles & Kelly Nadal Youth Centre at the Toronto Kiwanis Boys & Girls Clubhouse
101 Spruce Street
Now occupying a former church building, The Toronto Kiwanis Boys and Girls Club (TKBGC) first opened its doors to the Cabbagetown community in 1921. Since then, the TKBGC has provided support, development and engagement for children, youth, and their families. In 2012, the Miles and Kelly Nadal Youth Centre opened as part of the major renovations to the site to create a fully modernized, state-of-the-art facility. During this two year renovation period, the TKBGC opened six additional program sites in the community.

Former Home of Dr. Rowena Hume
226 Carlton Street
Dr. Rowena Hume was a founder and the first President of the Women's College Hospital when it opened in 1911. She held the position of Chief of Obstetrics and Gynaecology at the hospital for twenty years. A pioneer of planned parenthood programs, she formed the first Canadian Birth Control Clinic in Hamilton, Ontario in 1932. She was also actively involved in Alcoholics Anonymous, the Salvation Army's Harbour Light Centre, and the Fred Victor Mission. After retiring, she ran a private practice in Toronto. Hume Lane, just steps around the corner from her home and located off Ontario Street, was named in her honour.

Winchester Bar & Hotel
513-537 Parliament Street
The striking red brick Winchester Hotel (built in 1888) and Winchester Hall (built in 1880) have long been a landmark on the corner of Parliament and Winchester Streets. Designated with heritage status, the building exemplifies the Second Empire architectural style, with the interior of the hotel done in an Art Moderne style in the 1940s. Under this genteel veneer lies what used to be one of the toughest bars in the city, so much so that it was known as 'The Bucket of Blood'. Gangster Al Capone is also rumoured to have visited the bar & hotel to arrange the smuggling of liquor into the United States during prohibition. At the back of the building was Winchester Hall, a well-known jazz spot where Billie Holliday and Charlie Parker once performed.

Cabbagetown Youth Centre
2 Lancaster Avenue
Over the past 45 years, the Cabbagetown Youth Centre (CYC) has expanded to meet the growing needs of the community to provide a complete range of recreational, social and educational & skill development programs for ages ranging from newborns to seniors, while maintaining a specific focus on at-risk children and youth. CYC's mandate is to provide barrier-free access to a full range of programs otherwise not available to some of the most marginalized and high-need children, youth and families through the support and creation of sustainable programming to respond to gaps in services and combat risk factors.

Monica Wickeler Murals
439 Sherbourne Avenue
*Note: Private property. Please observe the residence from the sidewalk only. 'Re-Collect' is an intergenerational project onsite at Fudger House Long Term Care Home which brought together local youth from St. James Town and the senior residents. This community shared their stories through visual arts in a series of workshops and artwork from the workshops has been incorporated into the beautiful outdoor murals.

Explore Cabbagetown-South St. James Town

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Artists from various disciplines present messages of hope and resilience throughout the city in the form of text-based visual art installations.
Hiba Abdallah
Toronto Public Library -​ Lilian H. Smith Branch
239 College St, Toronto, ON M5T 1R5

Check out main street storefront art installations, in the neighbourhood or nearby, created by Local Arts Organizations and Business Improvement Areas across the City.

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We hope that you enjoyed exploring this Toronto neighbourhood and found many other points of interest along the way. While StrollTO highlights some of the 'hidden gems' in the neighbourhood, there may be others that could be included in a future edition. Would you like to share a point of interest that you discovered in the neighbourhood? Email us at [email protected].

Neighbourhood Stroll

The area occupied by Cabbagetown-South St. James Town has been called home by many varied communities over many generations. From the Don River at its eastern border to the modern city that lies to the west, this neighbourhood features an enchanting mix of old and the new, the past and the present. Stroll through the streets to learn about a visionary female doctor, bootlegging gangsters, and two of the most well-known cemeteries in the city. Step into unique shops and businesses in the Cabbagetown BIA, and enjoy the wide variety of amenities and art throughout the community.

Main Streets: Parliament Street, Carlton Street and Gerrard Street East
  1. St. James Cemetery
    635 Parliament Street
    St. James Cemetery is the oldest cemetery in the City of Toronto, in continual operation since 1844. The Anglican Church chose this large plot on the hill overlooking the ravine to be the cemetery as this location was originally several miles beyond most of the homes and shops in the city, and surrounded by farms. Architect John G. Howard was selected to design the layout of the grounds in 1842. The Chapel of St. James-The-Less was opened on the site in 1861, only 17 years after the opening of the cemetery. Designed by F.W. Cumberland, the Chapel has been a Toronto landmark ever since. The cemetery is the resting place of numerous prominent citizens and historical figures of Canada.
  2. Wellesley Cottages
    1 Wellesley Cottages
    *Note: Private property. Please observe the houses from the laneway only. During the 1851 Great Exhibition (in London, England), visitors flocked to view the new Model Dwellings, houses designed with health, sanitation and design at the forefront. These brick buildings became the ideal template for Victorian workers, and were emulated in various parts of the world. In 1865, Canadian Farmer magazine published the plans for a Cheap Country Dwelling House. This home took inspiration from the model dwellings, and is exemplified by a peak with ornamentation over the door, symmetrical windows and graceful appearance. The homes along Wellesley Crescent are based on these plans, and turned into a row of ideal workers cottages that represented the pinnacle in health and sanitation for the residents within. Today, this stretch of identical homes gives a glimpse into the modern process of neighbourhood planning.
  3. Overlooking Mouth of Castle Frank Brook
    500 Wellesley Street East
    This point, roughly where Bloor Street crosses the Don River, was a significant place of First Nations travel and sustenance. This point along the Don River is where the Davenport trail, perhaps the most prominent East-West First Nations trail in the Toronto area, crossed the Don River and turned South-Eastward towards what is now the Beaches neighborhood and then continuing Eastward along the Lake Ontario shoreline. Just west of this location, the Davenport trail was crossed by a North-South trail, one of the arms of the Toronto Carrying Place portage, that roughly followed the Don River watershed. These trails facilitated much First Nations and Métis movement through this area in the pre-colonial era, through the early fur trade, and into the nineteenth century. They also inspired the routes of their contemporary counterparts: Davenport Road and Yonge Street. In the Don River Valley at the point of the Davenport trail crossing, wild rice (minomeen, meaning the 'good seed' in Anishinaabemowin) used to grow. Minomeen has long been a very important and culturally meaningful part of Anishinaabe foodways and diets and its growth was encouraged throughout the Great Lakes watershed. These Minomeen beds also provided important habitat and food for ducks and other waterfowl, and so it is unsurprising that many migrating ducks frequented this area. When the Mississaugas were pushed out of their lands in Toronto and the subsequent increase in various forms of industrial development along the Don River, the minomeen fields disappeared. Anishinaabe people still plant and harvest minomeen today in other areas, but this practice is threatened by global corporations and settlers that dislike minomeen beds in the lake shallows by their cottages.
  4. Toronto Necropolis
    200 Winchester Street
    Opened in 1850, the Toronto Necropolis is one of the oldest cemeteries in the city. A necropolis is typically characterized by elaborate tombs and monuments, and are usually found outside of city limits. While this would have been the case in the nineteenth century, the grounds of the Toronto Necropolis today are firmly within the city boundaries. The vast array of sculptures, Victorian buildings, stained glass windows and distinctive High Victorian Gothic architecture all contribute to the picturesque nature of the site. The Necropolis is the final resting place for several well-known luminaries, including City Alderman William Peyton Hubbard, New Democratic Party leader Jack Layton, Second World War nurse Kay Christie, and Dr. Anderson Ruffin Abbott, the first Black-Canadian surgeon.
  5. Riverdale Farm
    201 Winchester Street
    The Riverdale Farm property was once owned by John Scadding, an early settler of the Town of York (now Toronto), who served as clerk to Upper Canada's first lieutenant governor, John Graves Simcoe. The City of Toronto purchased the land from Scadding in 1856. Riverdale Farm was built by the City as a tribute to Ontario's small, family farm heritage, and opened in 1978. The farm sits on the site of Toronto's first zoo, Riverdale Zoo, which closed in 1974. Visitors can still see some remnants of the old zoo, such as the zookeeper's residence, known as the Donnybook, and the Island House. Found just down the street from the farm is the Cabbagetown Farmers' Market, which offers local and sustainable food and production methods to the community.
  6. Miles & Kelly Nadal Youth Centre at the Toronto Kiwanis Boys & Girls Clubhouse
    101 Spruce Street
    Now occupying a former church building, The Toronto Kiwanis Boys and Girls Club (TKBGC) first opened its doors to the Cabbagetown community in 1921. Since then, the TKBGC has provided support, development and engagement for children, youth, and their families. In 2012, the Miles and Kelly Nadal Youth Centre opened as part of the major renovations to the site to create a fully modernized, state-of-the-art facility. During this two year renovation period, the TKBGC opened six additional program sites in the community.
  7. Former Home of Dr. Rowena Hume
    226 Carlton Street
    Dr. Rowena Hume was a founder and the first President of the Women's College Hospital when it opened in 1911. She held the position of Chief of Obstetrics and Gynaecology at the hospital for twenty years. A pioneer of planned parenthood programs, she formed the first Canadian Birth Control Clinic in Hamilton, Ontario in 1932. She was also actively involved in Alcoholics Anonymous, the Salvation Army's Harbour Light Centre, and the Fred Victor Mission. After retiring, she ran a private practice in Toronto. Hume Lane, just steps around the corner from her home and located off Ontario Street, was named in her honour.
  8. Winchester Bar & Hotel
    513-537 Parliament Street
    The striking red brick Winchester Hotel (built in 1888) and Winchester Hall (built in 1880) have long been a landmark on the corner of Parliament and Winchester Streets. Designated with heritage status, the building exemplifies the Second Empire architectural style, with the interior of the hotel done in an Art Moderne style in the 1940s. Under this genteel veneer lies what used to be one of the toughest bars in the city, so much so that it was known as 'The Bucket of Blood'. Gangster Al Capone is also rumoured to have visited the bar & hotel to arrange the smuggling of liquor into the United States during prohibition. At the back of the building was Winchester Hall, a well-known jazz spot where Billie Holliday and Charlie Parker once performed.
  9. Cabbagetown Youth Centre
    2 Lancaster Avenue
    Over the past 45 years, the Cabbagetown Youth Centre (CYC) has expanded to meet the growing needs of the community to provide a complete range of recreational, social and educational & skill development programs for ages ranging from newborns to seniors, while maintaining a specific focus on at-risk children and youth. CYC's mandate is to provide barrier-free access to a full range of programs otherwise not available to some of the most marginalized and high-need children, youth and families through the support and creation of sustainable programming to respond to gaps in services and combat risk factors.
  10. Monica Wickeler Murals
    439 Sherbourne Avenue
    *Note: Private property. Please observe the residence from the sidewalk only. 'Re-Collect' is an intergenerational project onsite at Fudger House Long Term Care Home which brought together local youth from St. James Town and the senior residents. This community shared their stories through visual arts in a series of workshops and artwork from the workshops has been incorporated into the beautiful outdoor murals.

Accessibility information: All points of interest on this stroll are visible from sidewalks. The Wellesley Cottages are accessible via a paved laneway from Wellesley Street. The Cabbagetown Youth Centre is accessible via Lancaster Avenue, a paved laneway. Both cemeteries have paved entrance areas, but access to some parts are on uneven ground.

Soundtracks of the City

From global superstars to local favourites and ones to watch, the Soundtracks of the City playlists all feature artists who have called Toronto home. Whether it’s a lyric about the neighborhood, an artist representing a cultural community, or a tie-in to the StrollTO itinerary itself, all the music reflects connections to an individual ward or the City as a whole.

Music was chosen based on an artist’s Spotify presence and each song’s broad appeal, as well as its associations with the cultures, languages and ethnicities that reflect Toronto’s neighborhoods and diverse music scene. Soundtracks of the City combines 425 songs that feature more than 500 different local artists or acts, showcasing songs in 23 different languages.