Dufferin Grove

Museum of Contemporary Art (MOCA)
158 Sterling Road
Previously located on Queen Street West, MOCA moved into this spectacular heritage-designated building in September of 2018. The building was originally constructed in 1919 and, for a time, was the tallest building in the city. It was originally a factory that produced aluminum products for the Second World War, and later produced kitchen tools, bottle caps, and car parts until it closed in 2006. MOCA works across all contemporary art forms to empower the local Toronto art scene, while informing the international. Numerous exhibits are offered throughout the year.

72 Sterling Road
72 Sterling Road
*Note: Private property. Please observe the building from the street only. The sweet smell of chocolate often in the air along Sterling Road is thanks to a factory, which has been a confectionary-producing site for over a century. It was purchased by Cowan Company Limited - a Toronto-based confectionary producer - in the 1890s where they produced products such as maple buds, a popular candy across Canada in the early part of the twentieth century. English chocolate giants Rowntree purchased the Cowan Company in 1926, who were in turn purchased by Nestle in 1988. The factory continues to be operated by Nestle to this day, producing products such as Smarties, Kit Kat, Aero, and Coffee Crisp. Notably, Coffee Crisp was invented in Toronto, and Canada remains the only country in which it is widely available.

Adrian Hayles Mural
1257 College Street
A new mural that depicts a bridge scene along the side of a local businesses, commissioned by the College West BIA.

MacGregor Playground
346 Lansdowne Avenue
A 1.4-hectare park on Lansdowne Avenue north of College Street that features a lit ball diamond, a field house, a basketball court, a wading pool and a children's playground.

Kent School
980 Dufferin Street
This heritage-designated school originally opened in 1908, and was named after Hebert E. Kent, a Toronto trustee who served for 21 years. It was constructed to alleviate overcrowding in the fast-growing area, as many other schools in the area were well over capacity. The land the school was built on was bought from Captain John E Denison, who in turn had received it as a gift from John Graves Simcoe. The school has since been transformed into a community centre, with tenants including the Toronto School of Art, the German International School of Toronto, and William Academy. The area surrounding Kent School is scheduled to be part of a massive commercial/residential redevelopment, but the school will be retained and continue to operate as a community centre.

Toronto Public Library - Bloor/Gladstone Branch
1101 Bloor Street West
This heritage-designated library branch was originally constructed by Toronto architectural firm Chapman and McGiffin in 1913 in a Beaux Arts adaptation of Italian Renaissance style. Notable architectural features include a low, hipped roof with extended eaves, Flemish bond brickwork with stone and terracotta detailing, and expansive round-arched windows. It was thought to be the largest library branch in Canada at the time it opened. The building has been renovated several times, most recently in 2009 when a large addition was added to the western side. Outside of the library not far from the front entrance, a poem entitled 'A Note to Readers' by Anne Michaels (Toronto's Poet Laureate from 2016 to 2019) is engraved in a plaque.

Dufferin Grove Park
875 Dufferin Street
This park is a 5.3-hectare park on Dufferin Street just south of Bloor Street West with large, mature forest canopy. It includes a sports field, basketball court, children's playground and, most interestingly, a reflexology footpath. At the north end of the park is the Dufferin Grove Park Artificial Ice Rink and Clubhouse. One notable feature of the park are the pieces of architectural ruins found in the trees on the western edge of the park. These are remnants of the Toronto Custom House, which stood at the southwest corner of Yonge Street and Front Street West from 1845 until it was demolished in 1919. These pieces had been languishing in a maintenance yard, before being moved here as part of artist Glen Threndyle's project 'Marsh Fountain'. The Jenna Morrison Memorial Reflexology Foot Path is the first of its kind in Canada, and is named after a local cyclist who was tragically struck and killed nearby.

Dragon Alley Community Garden
Dragon Alley Lane
*Note: Please follow Toronto Public Health's guidelines for visiting community & allotment gardens. A hidden community garden can be found in this alleyway off of Dufferin Street. Once a privately-owned but neglected greenspace, this land was purchased by the Toronto Parking Authority (TPA) in 2009 and converted into a 34-space lot. Landscaped planters were set up at either end of the new lot, and neighbourhood residents who were upset at losing their greenspace took it upon themselves to plant vegetables in the garden. TPA threatened to uproot the garden, but a compromise was brokered by the local Councillor between the TPA and neighbourhood residents that allowed it to stay. It was provided with its official moniker 'Dragon Alley Community Garden' during a naming ceremony in May 2013.

EGR 'Reach for the Skies' Mural
1114 College Street
This spectacular mural entitled 'Reach for the Skies' takes over the entire side of a building, depicting a lively street scene with street performers, skateboarders, and locals enjoying a neighbourhood stroll.

The Blue Room
Northwest corner of College Street & Dovercourt Road
The northwest corner of College Street and Dovercourt Road is noticeably covered in blue paint, with blue lighting that further accentuates it during the nighttime hours. This installation is part of a larger project by artist Stanislav Jurkovic, who describes the project as, '...the creation of a space within a space...through an act of subtracting all that is 'aggregated background' by the addition of non-discriminating colour.' The other two 'blue rooms' are located at the intersections of College Street and Ossington Avenue, and College Street and Roxton Road. The lamps mostly project a turquoise-like colour, though every hour they shine full blue for about 60 seconds, and also project white light onto the surface every half hour or so.

The Matador Ballroom
466 Dovercourt Road
This building was previously home to The Matador, a legendary live music venue that existed here for over forty years. The original building dates back much longer than that (all the way to 1915) when it was constructed as a community dance hall. It operated as a bowling alley for numerous years, until it was converted into the live music venue it's presently known for in 1964. Over the years, The Matador hosted a number of noteworthy artists, including Joni Mitchell and Stompin' Tom Connors. Leonard Cohen's 1992 hit song 'Closing Time' is rumoured to have been written about The Matador, and Cohen filmed the music video for the song there. The venue officially closed in 2007. A new owner attempted to revive The Matador in the 2010s, but those efforts were ultimately unsuccessful. The building is now planned to be demolished and turn into a condominium, though the developers intend to keep the famous sign affixed out front.

Dovercourt-St. Paul's Presbyterian Church
700 Dovercourt Road
This heritage-designated church was constructed in 1905 and designed by William Gregg, who also designed a few other churches in the area. An addition added to the building in 1910 was designed by architectural firm Simpson and Young and became a Sunday school. Legendary Toronto Maple Leafs executive Conn Smythe was a teacher at this Sunday school, and the Maple Leafs players even used the gymnasium in the building as a practice facility in the 1940s. The Sunday school addition has since been converted into a residential loft building, while the church continues to offer services to two separate congregations.

Explore Dufferin Grove

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.

We want to hear from you! Click here to complete a short survey

Suppport small business owners by Shopping Small.

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.
Women Paint
Toronto Public Library: Dufferin/St. Clair Branch
1625 Dufferin St, Toronto, ON M6H 3L9

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 beautiful west-end neighbourhood with a strong sense of community is centred around Dufferin Grove Park, a wonderful green space with plenty of amenities that is a central meeting point for residents and visitors alike. There are plenty of great shops, bars, restaurants, and cafes to be found in the numerous BIAs this stroll touches on, including Bloorcourt Village, Bloordale Village, College West, College Promenade, and Little Portugal on Dundas.

Main Streets: Bloor Street West, College Street and Dufferin Street
  1. Museum of Contemporary Art (MOCA)
    158 Sterling Road
    Previously located on Queen Street West, MOCA moved into this spectacular heritage-designated building in September of 2018. The building was originally constructed in 1919 and, for a time, was the tallest building in the city. It was originally a factory that produced aluminum products for the Second World War, and later produced kitchen tools, bottle caps, and car parts until it closed in 2006. MOCA works across all contemporary art forms to empower the local Toronto art scene, while informing the international. Numerous exhibits are offered throughout the year.
  2. 72 Sterling Road
    72 Sterling Road
    *Note: Private property. Please observe the building from the street only. The sweet smell of chocolate often in the air along Sterling Road is thanks to a factory, which has been a confectionary-producing site for over a century. It was purchased by Cowan Company Limited - a Toronto-based confectionary producer - in the 1890s where they produced products such as maple buds, a popular candy across Canada in the early part of the twentieth century. English chocolate giants Rowntree purchased the Cowan Company in 1926, who were in turn purchased by Nestle in 1988. The factory continues to be operated by Nestle to this day, producing products such as Smarties, Kit Kat, Aero, and Coffee Crisp. Notably, Coffee Crisp was invented in Toronto, and Canada remains the only country in which it is widely available.
  3. Adrian Hayles Mural
    1257 College Street
    A new mural that depicts a bridge scene along the side of a local businesses, commissioned by the College West BIA.
  4. MacGregor Playground
    346 Lansdowne Avenue
    A 1.4-hectare park on Lansdowne Avenue north of College Street that features a lit ball diamond, a field house, a basketball court, a wading pool and a children's playground.
  5. Kent School
    980 Dufferin Street
    This heritage-designated school originally opened in 1908, and was named after Hebert E. Kent, a Toronto trustee who served for 21 years. It was constructed to alleviate overcrowding in the fast-growing area, as many other schools in the area were well over capacity. The land the school was built on was bought from Captain John E Denison, who in turn had received it as a gift from John Graves Simcoe. The school has since been transformed into a community centre, with tenants including the Toronto School of Art, the German International School of Toronto, and William Academy. The area surrounding Kent School is scheduled to be part of a massive commercial/residential redevelopment, but the school will be retained and continue to operate as a community centre.
  6. Toronto Public Library - Bloor/Gladstone Branch
    1101 Bloor Street West
    This heritage-designated library branch was originally constructed by Toronto architectural firm Chapman and McGiffin in 1913 in a Beaux Arts adaptation of Italian Renaissance style. Notable architectural features include a low, hipped roof with extended eaves, Flemish bond brickwork with stone and terracotta detailing, and expansive round-arched windows. It was thought to be the largest library branch in Canada at the time it opened. The building has been renovated several times, most recently in 2009 when a large addition was added to the western side. Outside of the library not far from the front entrance, a poem entitled 'A Note to Readers' by Anne Michaels (Toronto's Poet Laureate from 2016 to 2019) is engraved in a plaque.
  7. Dufferin Grove Park
    875 Dufferin Street
    This park is a 5.3-hectare park on Dufferin Street just south of Bloor Street West with large, mature forest canopy. It includes a sports field, basketball court, children's playground and, most interestingly, a reflexology footpath. At the north end of the park is the Dufferin Grove Park Artificial Ice Rink and Clubhouse. One notable feature of the park are the pieces of architectural ruins found in the trees on the western edge of the park. These are remnants of the Toronto Custom House, which stood at the southwest corner of Yonge Street and Front Street West from 1845 until it was demolished in 1919. These pieces had been languishing in a maintenance yard, before being moved here as part of artist Glen Threndyle's project 'Marsh Fountain'. The Jenna Morrison Memorial Reflexology Foot Path is the first of its kind in Canada, and is named after a local cyclist who was tragically struck and killed nearby.
  8. Dragon Alley Community Garden
    Dragon Alley Lane
    *Note: Please follow Toronto Public Health's guidelines for visiting community & allotment gardens. A hidden community garden can be found in this alleyway off of Dufferin Street. Once a privately-owned but neglected greenspace, this land was purchased by the Toronto Parking Authority (TPA) in 2009 and converted into a 34-space lot. Landscaped planters were set up at either end of the new lot, and neighbourhood residents who were upset at losing their greenspace took it upon themselves to plant vegetables in the garden. TPA threatened to uproot the garden, but a compromise was brokered by the local Councillor between the TPA and neighbourhood residents that allowed it to stay. It was provided with its official moniker 'Dragon Alley Community Garden' during a naming ceremony in May 2013.
  9. EGR 'Reach for the Skies' Mural
    1114 College Street
    This spectacular mural entitled 'Reach for the Skies' takes over the entire side of a building, depicting a lively street scene with street performers, skateboarders, and locals enjoying a neighbourhood stroll.
  10. The Blue Room
    Northwest corner of College Street & Dovercourt Road
    The northwest corner of College Street and Dovercourt Road is noticeably covered in blue paint, with blue lighting that further accentuates it during the nighttime hours. This installation is part of a larger project by artist Stanislav Jurkovic, who describes the project as, '...the creation of a space within a space...through an act of subtracting all that is 'aggregated background' by the addition of non-discriminating colour.' The other two 'blue rooms' are located at the intersections of College Street and Ossington Avenue, and College Street and Roxton Road. The lamps mostly project a turquoise-like colour, though every hour they shine full blue for about 60 seconds, and also project white light onto the surface every half hour or so.
  11. The Matador Ballroom
    466 Dovercourt Road
    This building was previously home to The Matador, a legendary live music venue that existed here for over forty years. The original building dates back much longer than that (all the way to 1915) when it was constructed as a community dance hall. It operated as a bowling alley for numerous years, until it was converted into the live music venue it's presently known for in 1964. Over the years, The Matador hosted a number of noteworthy artists, including Joni Mitchell and Stompin' Tom Connors. Leonard Cohen's 1992 hit song 'Closing Time' is rumoured to have been written about The Matador, and Cohen filmed the music video for the song there. The venue officially closed in 2007. A new owner attempted to revive The Matador in the 2010s, but those efforts were ultimately unsuccessful. The building is now planned to be demolished and turn into a condominium, though the developers intend to keep the famous sign affixed out front.
  12. Dovercourt-St. Paul's Presbyterian Church
    700 Dovercourt Road
    This heritage-designated church was constructed in 1905 and designed by William Gregg, who also designed a few other churches in the area. An addition added to the building in 1910 was designed by architectural firm Simpson and Young and became a Sunday school. Legendary Toronto Maple Leafs executive Conn Smythe was a teacher at this Sunday school, and the Maple Leafs players even used the gymnasium in the building as a practice facility in the 1940s. The Sunday school addition has since been converted into a residential loft building, while the church continues to offer services to two separate congregations.

Accessibility information: Most points of interest on this stroll are viewable from the street. Dufferin Grove Park has mostly paved paths, but does contain some unpaved areas and stairs.

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.