Leaside Bennington

Serena Gundy Park
58 Rykert Crescent
This beautiful park located in the West Don River Valley was named in honour of the first wife of James H. Gundy, who donated land from his estate in 1960. Gundy did so with the understanding that $200,000 would be spent on park improvements, and that a memorial for his wife would be erected. A bronze plaque stands near the entrance at Broadway Avenue and Rykert Crescent honouring Serena Gundy and the transfer of this land for all to enjoy. The park features several walking and hiking trails, lovely bridges over the Don River, picnic sites, sports fields for cricket, rugby, soccer, and field hockey, and horse stables.

Canada's First Air Mail Plaque
Intersection of Broadway Avenue and Brentcliffe Road
*Note: This plaque is located in a traffic island. Please cross the street at the stop sign to view it. A plaque in the traffic island at Broadway Avenue and Brentcliffe Road notes that the former Leaside Aerodrome was the site of the first air mail delivery in Canada. Royal Air Force pilots took off from Montreal on June 24, 1918, battling terrible weather along the way, and made two stops, in Kingston and Deseronto, before arriving here in the afternoon. The flight was meant to demonstrate that aviation was the way of the future. The Leaside Aerodrome was built starting in 1917, and covered the area that roughly corresponds to today's Sutherland Drive to the west, the Don River to the east, Wicksteed Avenue to the south, and Broadway Avenue to the north. As Leaside began to develop, many pieces of the airport were demolished, with the last hangar meeting its demise in 1971.

Elicser Mural
826 Eginton Avenue East
This wonderful mural was painted by artist Elicser Elliott on the side of this building in August 2017. Elliott has been a huge part of Toronto's street art community for decades. Born in Montreal, Elliott spent much of his youth on the island of St. Vincent, returning to Canada and ultimately developing his artistic talents at the Etobicoke School for the Arts and Sheridan College. Elliott's work can be found in many locations across Toronto, and has been featured in multiple publications, the Art Gallery of Ontario, and the Royal Ontario Museum.

Howard Talbot Park
635 Eglinton Avenue East
This park is named after Howard Talbot, the Mayor of the former Town of Leaside from 1938 to 1947. Talbot was responsible for developing much of Leaside in the late 1920s, buying up land and building homes on several streets nearby. He was elected Mayor in 1938, and presided over the period where Leaside transformed from being a small company town to a bustling suburb of Toronto. He was also instrumental in developing several important neighbourhood structures, such as Leaside Town Hall and Leaside Memorial Gardens. Talbot arranged for the purchase of land for the park that is named after him. Today the park features two ball diamonds including one with lights, a multipurpose sports field and track, two outdoor tennis courts, a splash pad and children's playground. Located at the east end of the park is the Leaside Lawn Bowling Club.

Thomas G. Elgie House
262 Bessborough Drive
*Note: Private property. Please observe the house from the street only. This heritage-designated home - the oldest in Leaside - is one of three remaining in the area that predate the incorporation of Leaside as a town in 1913. It was built circa 1883 as a farmhouse on the estate of Thomas G. Elgie, who was a farmer and realtor. The Elgie estate covered about 200 acres of land southeast of present-day Bayview Avenue and Eglinton Avenue East for many years. The home stands out as a physical reminder of the area's agricultural past. The two other remaining homes that predate Leaside's incorporation are located nearby at 33 Heather Road and 201 Sutherland Drive.

1783-1785 Bayview Avenue
1783-1785 Bayview Avenue
*Note: Private property. Please observe the building from the street only. This small heritage-designated apartment building is one of 10 in a row along Bayview Avenue that are architecturally unique in character. They were constructed by Howard Talbot, a developer who later became Mayor of Leaside and whom nearby Howard Talbot Park is named after. This building was erected in 1936-37 in a Tudor Revival variation on Arts and Crafts, featuring paired bay windows with stone bases, double hung sash windows, and a front door with a Tudor arch stone. The architectural design of the building is reflective of Leaside's development as a master-planned 'Garden Suburb' in the first half of the twentieth century.

Agnes Macphail House
720 Millwood Road
*Note: Private property. Please observe the house from the street only. This heritage-designated house was once the home of Agnes Macphail, who was Canada's first female Member of Parliament. After her first victory in 1921, she went on to win five successive elections, including becoming MPP for York East in 1943. Macphail is recognized for her contributions to health insurance, low rental housing, workers' rights, penal reform, women's rights, and seniors' pensions. As a member of the World Disarmament Committee, she was also the first Canadian woman delegate to the League of Nations. The house was constructed in 1937 in Modernist style, and Macphail moved into it in 1948.

Garden Court Apartments
1477 Bayview Avenue
*Note: Private property. Please observe the house from the street only. One of several garden apartment blocks constructed around Leaside, the heritage-designated Garden Court Apartments are especially noteworthy due to their scale and design excellence. They were constructed in Art Moderne style in 1939-41, designed by architectural firm Forsey Page & Steele, with landscape design provided by Dunington-Grubb and Stensson. The unique design features 10 apartment blocks placed around the perimeter of a large courtyard, and is reported to be the first in Canada to feature streamlined Art Moderne detailing and materials, both of which were new at this time. Forsey Page & Steele won the inaugural Massey Medal for Architecture in 1950 for this design.

Trace Manes Park
110 Rumsey Road
Leaside was originally developed as a master planned town by the Canadian National Railroad with a design by landscape architect Frederick Todd Gage in 1912. Gage designed Leaside based on the principles of the garden city movement popular at the time, featuring curvilinear streets, and an industrial area distinctly separated from the residential zones. Gage's initial plan called for several small parks to be scattered throughout the town, though this never fully materialized. To compensate for this, Leaside Town Council purchased lots for three public parks, including Trace Manes Park, which is now the green centre of the community. McRae Drive and Rumsey Road gently curve around the park, providing a visual manifestation of Gage's original curvilinear street design of Leaside. Trace Manes Park features a wading pool that is a great spot for a family-friendly day, as well as a baseball diamond, tennis courts, a playground, and Toronto Public Library's Leaside Branch.

Leaside Municipal Building
231-235 McRae Drive
*Note: This is an active fire station. Please do not block the driveway. This heritage-designated building was once the site of the municipal offices of the Town of Leaside. Leaside was officially incorporated as a town in 1913 and remained independent until becoming part of the Borough of East York from 1967 to 1998. The building - which opened in 1949 - was designed by architectural firm Hanks and Irwin to seamlessly blend in with the surrounding landscape of homes and apartments, reflecting much of Leaside's original design. The building is considered to be a fine example of Modern Classicism, featuring exterior walls clad with buff brick and trimmed with stone, a frontispiece with a parapet and keystone, and a pair of Medallions with a Classical motif. The building has since been converted to commercial usage, though Toronto Fire Station 321 still operates out of it.

Durant Motor Company Building
150 Laird Drive
This heritage-designated building is reflective of the industrial history of the area along Laird Drive. When Leaside was originally developed as a company town by the Canadian Northern Railway, Frederick Todd Gage specifically marked the south and east areas of his town plan for railway and industrial usages. One of the many industrial companies that set up shop in this area was the Durant Motor Company, who constructed this building as its offices in 1928. Durant had a manufacturing plant located across Laird in an old munitions factory and became the third largest domestic producer of automobiles in Canada by 1929. Durant closed several years later and a number of other tenants have called the building home since. The building is an excellent example of Late Gothic Revival style architecture. It is currently subject to substantial redevelopment plans that could see its structure significantly altered, though the front-facing facade of the building should be maintained.

Leaside Memorial Gardens
1073 Millwood Road
Leaside Memorial Gardens has been a community landmark for over 60 years, offering a double-pad ice rink, banquet room, indoor swimming pool, and curling rink. The facility originally opened in 1951 on land that was donated by the Lea family, and was named in honour of Second World War veterans from the Town of Leaside. Seven NHL hockey players played here in their youth, including Peter Mahovlich Jr., Brad Selwood, Terry Caffery, Paul Gardner, Dave Gardner, Tom Edur, and Mike McEwen. All of these players' sweaters hang above the rafters in the arena. Peter Mahovlich Sr., an immigrant from Yugoslavia and the father of Peter Jr. and Maple Leafs' great Frank Mahovlich, was the Zamboni driver and skate sharpener at the arena for over 20 years. A plaque hangs outside a dressing room to commemorate his service to the community.

Crothers Woods
27 Redway Road
With around 10 km of natural trails, a diverse bird population and some spots offering a spectacular view of the Toronto skyline, Crothers Woods is a popular escape into nature. Crothers Woods offers approximately 9 km of multi-use, one-metre wide dirt trails. These trails include some steep sections and are rated as intermediate level trails. Crothers Woods is an Environmentally Significant Area due to its diverse, mature and relatively undisturbed forest, and the presence of wildflowers and tree species that are rare in the Toronto region. One unique feature of the park is a massive, strange staircase that leads down into the valley from near the Redway Road entrance and reaches a dead end at the gates of the North Toronto Sewage Treatment Plant. *Note: The stairway from Redway Road may not be maintained.

Evergreen Brick Works
550 Bayview Avenue
Don Valley Brick Works was founded in 1889 and was operational for almost a century. The bricks were used to build many significant Toronto landmarks such as Massey Hall and Casa Loma. Evergreen, an environmental development organization, transformed the existing buildings, kilns, and quarry into the Evergreen Brick Works and surrounding parklands, which opened in 2010. The site is home to the Young Welcome Centre, garden and farmers' markets, a bike shop and cafe. The main facility, the Centre for Green Cities, is an educational centre teaching sustainability and stewardship of healthy urban environments. There is also an Indigenous Urban Agricultural Garden that focuses on growing plants and food native to Toronto and utilizes First Nations' gardening techniques such as 'Three Sisters', which uses the symbiotic relationship between three different types of vegetables to help them grow. There's also an abundance of public art to see including 'Nestled' by Jana Ostermann, a hand-woven light fixture that resembles a bird's nest.

Don Valley Brick Works Park
550 Bayview Avenue
Once a former quarry, Don Valley Brick Works Park is now a City of Toronto flagship natural environment park. It is considered a model for urban ecosystem planning given its extensive landscape restoration, re-naturalization, wetland re-establishment, and adaptive management. Take a minute to stroll through the park and wetlands, which support a variety of animals such as painted and snapping turtles, great blue herons and beavers. Fabulous views over the surrounding area can be found at the Governor's Lookout within the park. Evergreen Brick Works offers private guided walks of the park, focusing on the area's history and ecology.

Explore Leaside Bennington

Now is the time for residents to experience all that tourists have been raving about for years. Discover shops, stops, places and spaces on city main streets. Stay curious, Toronto.

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Don't Miss

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: Mount Pleasant Branch
599 Mt Pleasant Rd, Toronto, ON M4S 2M5

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

Painting Icon StrollTO Guided Walks:

On select weekend dates, join guided walks and discover the diverse histories and cultural significance behind neighbourhood landmarks and attractions.
Learn more and register.

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

This neighbourhood spans a large swathe of land close to the Don River, and features the historic area of Leaside, as well as some of the most spectacular ravine landscapes available in the city. Leaside continues to maintain its historic character as a product of the Garden City movement, with beautiful homes, architecturally-stunning apartment blocks, gently curving streets, serene green spaces, as well as remnants of an industrial past. Explorers of the vast green spaces along the Don River throughout this area will be transported into a lush, natural world that seems far away from the city. Fantastic local businesses can be found throughout the area, particularly along Bayview Avenue in the Bayview-Leaside BIA.

Main Streets: Bayview Avenue, Eglinton Avenue East, Laird Drive
  1. Serena Gundy Park
    58 Rykert Crescent
    This beautiful park located in the West Don River Valley was named in honour of the first wife of James H. Gundy, who donated land from his estate in 1960. Gundy did so with the understanding that $200,000 would be spent on park improvements, and that a memorial for his wife would be erected. A bronze plaque stands near the entrance at Broadway Avenue and Rykert Crescent honouring Serena Gundy and the transfer of this land for all to enjoy. The park features several walking and hiking trails, lovely bridges over the Don River, picnic sites, sports fields for cricket, rugby, soccer, and field hockey, and horse stables.
  2. Canada's First Air Mail Plaque
    Intersection of Broadway Avenue and Brentcliffe Road
    *Note: This plaque is located in a traffic island. Please cross the street at the stop sign to view it. A plaque in the traffic island at Broadway Avenue and Brentcliffe Road notes that the former Leaside Aerodrome was the site of the first air mail delivery in Canada. Royal Air Force pilots took off from Montreal on June 24, 1918, battling terrible weather along the way, and made two stops, in Kingston and Deseronto, before arriving here in the afternoon. The flight was meant to demonstrate that aviation was the way of the future. The Leaside Aerodrome was built starting in 1917, and covered the area that roughly corresponds to today's Sutherland Drive to the west, the Don River to the east, Wicksteed Avenue to the south, and Broadway Avenue to the north. As Leaside began to develop, many pieces of the airport were demolished, with the last hangar meeting its demise in 1971.
  3. Elicser Mural
    826 Eginton Avenue East
    This wonderful mural was painted by artist Elicser Elliott on the side of this building in August 2017. Elliott has been a huge part of Toronto's street art community for decades. Born in Montreal, Elliott spent much of his youth on the island of St. Vincent, returning to Canada and ultimately developing his artistic talents at the Etobicoke School for the Arts and Sheridan College. Elliott's work can be found in many locations across Toronto, and has been featured in multiple publications, the Art Gallery of Ontario, and the Royal Ontario Museum.
  4. Howard Talbot Park
    635 Eglinton Avenue East
    This park is named after Howard Talbot, the Mayor of the former Town of Leaside from 1938 to 1947. Talbot was responsible for developing much of Leaside in the late 1920s, buying up land and building homes on several streets nearby. He was elected Mayor in 1938, and presided over the period where Leaside transformed from being a small company town to a bustling suburb of Toronto. He was also instrumental in developing several important neighbourhood structures, such as Leaside Town Hall and Leaside Memorial Gardens. Talbot arranged for the purchase of land for the park that is named after him. Today the park features two ball diamonds including one with lights, a multipurpose sports field and track, two outdoor tennis courts, a splash pad and children's playground. Located at the east end of the park is the Leaside Lawn Bowling Club.
  5. Thomas G. Elgie House
    262 Bessborough Drive
    *Note: Private property. Please observe the house from the street only. This heritage-designated home - the oldest in Leaside - is one of three remaining in the area that predate the incorporation of Leaside as a town in 1913. It was built circa 1883 as a farmhouse on the estate of Thomas G. Elgie, who was a farmer and realtor. The Elgie estate covered about 200 acres of land southeast of present-day Bayview Avenue and Eglinton Avenue East for many years. The home stands out as a physical reminder of the area's agricultural past. The two other remaining homes that predate Leaside's incorporation are located nearby at 33 Heather Road and 201 Sutherland Drive.
  6. 1783-1785 Bayview Avenue
    1783-1785 Bayview Avenue
    *Note: Private property. Please observe the building from the street only. This small heritage-designated apartment building is one of 10 in a row along Bayview Avenue that are architecturally unique in character. They were constructed by Howard Talbot, a developer who later became Mayor of Leaside and whom nearby Howard Talbot Park is named after. This building was erected in 1936-37 in a Tudor Revival variation on Arts and Crafts, featuring paired bay windows with stone bases, double hung sash windows, and a front door with a Tudor arch stone. The architectural design of the building is reflective of Leaside's development as a master-planned 'Garden Suburb' in the first half of the twentieth century.
  7. Agnes Macphail House
    720 Millwood Road
    *Note: Private property. Please observe the house from the street only. This heritage-designated house was once the home of Agnes Macphail, who was Canada's first female Member of Parliament. After her first victory in 1921, she went on to win five successive elections, including becoming MPP for York East in 1943. Macphail is recognized for her contributions to health insurance, low rental housing, workers' rights, penal reform, women's rights, and seniors' pensions. As a member of the World Disarmament Committee, she was also the first Canadian woman delegate to the League of Nations. The house was constructed in 1937 in Modernist style, and Macphail moved into it in 1948.
  8. Garden Court Apartments
    1477 Bayview Avenue
    *Note: Private property. Please observe the house from the street only. One of several garden apartment blocks constructed around Leaside, the heritage-designated Garden Court Apartments are especially noteworthy due to their scale and design excellence. They were constructed in Art Moderne style in 1939-41, designed by architectural firm Forsey Page & Steele, with landscape design provided by Dunington-Grubb and Stensson. The unique design features 10 apartment blocks placed around the perimeter of a large courtyard, and is reported to be the first in Canada to feature streamlined Art Moderne detailing and materials, both of which were new at this time. Forsey Page & Steele won the inaugural Massey Medal for Architecture in 1950 for this design.
  9. Trace Manes Park
    110 Rumsey Road
    Leaside was originally developed as a master planned town by the Canadian National Railroad with a design by landscape architect Frederick Todd Gage in 1912. Gage designed Leaside based on the principles of the garden city movement popular at the time, featuring curvilinear streets, and an industrial area distinctly separated from the residential zones. Gage's initial plan called for several small parks to be scattered throughout the town, though this never fully materialized. To compensate for this, Leaside Town Council purchased lots for three public parks, including Trace Manes Park, which is now the green centre of the community. McRae Drive and Rumsey Road gently curve around the park, providing a visual manifestation of Gage's original curvilinear street design of Leaside. Trace Manes Park features a wading pool that is a great spot for a family-friendly day, as well as a baseball diamond, tennis courts, a playground, and Toronto Public Library's Leaside Branch.
  10. Leaside Municipal Building
    231-235 McRae Drive
    *Note: This is an active fire station. Please do not block the driveway. This heritage-designated building was once the site of the municipal offices of the Town of Leaside. Leaside was officially incorporated as a town in 1913 and remained independent until becoming part of the Borough of East York from 1967 to 1998. The building - which opened in 1949 - was designed by architectural firm Hanks and Irwin to seamlessly blend in with the surrounding landscape of homes and apartments, reflecting much of Leaside's original design. The building is considered to be a fine example of Modern Classicism, featuring exterior walls clad with buff brick and trimmed with stone, a frontispiece with a parapet and keystone, and a pair of Medallions with a Classical motif. The building has since been converted to commercial usage, though Toronto Fire Station 321 still operates out of it.
  11. Durant Motor Company Building
    150 Laird Drive
    This heritage-designated building is reflective of the industrial history of the area along Laird Drive. When Leaside was originally developed as a company town by the Canadian Northern Railway, Frederick Todd Gage specifically marked the south and east areas of his town plan for railway and industrial usages. One of the many industrial companies that set up shop in this area was the Durant Motor Company, who constructed this building as its offices in 1928. Durant had a manufacturing plant located across Laird in an old munitions factory and became the third largest domestic producer of automobiles in Canada by 1929. Durant closed several years later and a number of other tenants have called the building home since. The building is an excellent example of Late Gothic Revival style architecture. It is currently subject to substantial redevelopment plans that could see its structure significantly altered, though the front-facing facade of the building should be maintained.
  12. Leaside Memorial Gardens
    1073 Millwood Road
    Leaside Memorial Gardens has been a community landmark for over 60 years, offering a double-pad ice rink, banquet room, indoor swimming pool, and curling rink. The facility originally opened in 1951 on land that was donated by the Lea family, and was named in honour of Second World War veterans from the Town of Leaside. Seven NHL hockey players played here in their youth, including Peter Mahovlich Jr., Brad Selwood, Terry Caffery, Paul Gardner, Dave Gardner, Tom Edur, and Mike McEwen. All of these players' sweaters hang above the rafters in the arena. Peter Mahovlich Sr., an immigrant from Yugoslavia and the father of Peter Jr. and Maple Leafs' great Frank Mahovlich, was the Zamboni driver and skate sharpener at the arena for over 20 years. A plaque hangs outside a dressing room to commemorate his service to the community.
  13. Crothers Woods
    27 Redway Road
    With around 10 km of natural trails, a diverse bird population and some spots offering a spectacular view of the Toronto skyline, Crothers Woods is a popular escape into nature. Crothers Woods offers approximately 9 km of multi-use, one-metre wide dirt trails. These trails include some steep sections and are rated as intermediate level trails. Crothers Woods is an Environmentally Significant Area due to its diverse, mature and relatively undisturbed forest, and the presence of wildflowers and tree species that are rare in the Toronto region. One unique feature of the park is a massive, strange staircase that leads down into the valley from near the Redway Road entrance and reaches a dead end at the gates of the North Toronto Sewage Treatment Plant. *Note: The stairway from Redway Road may not be maintained.
  14. Evergreen Brick Works
    550 Bayview Avenue
    Don Valley Brick Works was founded in 1889 and was operational for almost a century. The bricks were used to build many significant Toronto landmarks such as Massey Hall and Casa Loma. Evergreen, an environmental development organization, transformed the existing buildings, kilns, and quarry into the Evergreen Brick Works and surrounding parklands, which opened in 2010. The site is home to the Young Welcome Centre, garden and farmers' markets, a bike shop and cafe. The main facility, the Centre for Green Cities, is an educational centre teaching sustainability and stewardship of healthy urban environments. There is also an Indigenous Urban Agricultural Garden that focuses on growing plants and food native to Toronto and utilizes First Nations' gardening techniques such as 'Three Sisters', which uses the symbiotic relationship between three different types of vegetables to help them grow. There's also an abundance of public art to see including 'Nestled' by Jana Ostermann, a hand-woven light fixture that resembles a bird's nest.
  15. Don Valley Brick Works Park
    550 Bayview Avenue
    Once a former quarry, Don Valley Brick Works Park is now a City of Toronto flagship natural environment park. It is considered a model for urban ecosystem planning given its extensive landscape restoration, re-naturalization, wetland re-establishment, and adaptive management. Take a minute to stroll through the park and wetlands, which support a variety of animals such as painted and snapping turtles, great blue herons and beavers. Fabulous views over the surrounding area can be found at the Governor's Lookout within the park. Evergreen Brick Works offers private guided walks of the park, focusing on the area's history and ecology.

Accessibility information: Most points of interest in this stroll are viewable from the street. Significant portions of Serena Gundy Park, Crothers Woods, and Don Valley Brick Works Park contain steep hills, stairs, and unpaved paths. Those wishing to move between Leaside Memorial Gardens and Evergreen Brick Works while avoiding Crothers Woods can do so by proceeding across the Millwood Overpass to Pape Avenue, turning right on O'Connor Drive, turning left on Broadview Avenue, and then turning right on Pottery Road to Bayview Avenue.

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.