Oakwood Village

Oakwood and St. Clair Streetcar Loop
Oakwood Avenue and St. Clair Avenue West
Oakwood developed as a streetcar suburb, a residential community strongly shaped by the use of streetcar lines. As the area grew and businesses opened on Eglinton Avenue, the Township of York entered an agreement with the Toronto Transit Commission (TTC) to establish the Oakwood and Rogers Road Streetcars in 1924 to meet growing ridership demands. The TTC charged an extra fare when the streetcar crossed the city limits. Today, neither streetcar line is in operation, but the loop remains and is used for the St. Clair streetcar instead.

Oakwood Village Library and Arts Centre
341 Oakwood Avenue
Oakwood Village Public Library and Arts Centre is a community hub with educational programs for children, youth and adults, exhibition space for monthly shows by local artists, a music practice room, and an auditorium.

Karen Roberts Artbox
529 Vaughan Road
Artist Karen Roberts has a personal connection to the Vaughan Road Academy represented on this artbox, having attended the school herself. The design uses the school's colours (red, blue and gold) and includes the school's V logo in the centre. Roberts also painted the school's mascot, various sports figures, books and paper airplanes. After serving the community for nine decades, the Vaughan Road Academy closed in 2017 due to low enrollment. Graduates of the school include actor Neve Campbell, rapper/actor Aubrey 'Drake' Graham, actor William Hutt and former Toronto Poet Laureate Anne Michaels.

Laughlin Park
420 Atlas Avenue
A small park near Vaughan Road and Oakwood Avenue that features a children's playground.

Palm Tree
Intersection of Oakwood Avenue and Vaughan Road
In 2010, a 4.9-metre steel palm tree was installed on the traffic island at the corner of Oakwood Avenue and Vaughan Road. Oakwood Village is home to many residents from Caribbean countries, for which the palm tree is a native species. The tree is symbolic of the roots put down by the Caribbean community.

Dan Bergeron 'A Common Thread' Mural
Intersection of Oakwood Avenue and Vaughan Road
This new mural on the benches in the Vaughan Road and Oakwood Avenue traffic island was commissioned by the Oakwood Village BIA and Nia Centre for the Arts. It was painted by visual artist Dan Bergeron in conjunction with two emerging Black artists selected by the Nia Centre for the Arts. It depicts a quilting pattern, meant to display memories and stories from the neighbourhood.

Nia Centre for the Arts
524 Oakwood Avenue
Nia Centre for the Arts supports local artists and showcases art from across the African Diaspora through exhibitions and festivals. The centre focuses on creating opportunities for young people and emerging artists by offering arts-based workshops, programs, events and camps. Nia is a Swahili word for purpose, and the organization is dedicated to supporting and highlighting those who have found purpose through art. The centre is currently undergoing a redevelopment process that will add a 160-seat performance theatre, co-working spaces, digital arts incubation studios, recording & visual arts studios, and community workspaces.

UNISON Building Mosaic
501 Oakwood Avenue
A beautiful tiled mosaic along the raised landscaped edge and retaining wall of 501 Oakwood Avenue welcomes people to the neighbourhood with an expression of the word unity in several languages. The artistic creation and direction was led by Art Starts (founded in the neighbourhood) and Red Pepper Spectacle Arts. Both art organizations continue to have an impactful presence in the city. After much community advocacy, 501 Oakwood Avenue opened as a Community Health Centre in 2019.

Share Magazine
658 Vaughan Road
This building houses the offices of Share Magazine, a weekly community newspaper that serves the Black and Caribbean community in the Greater Toronto Area (GTA). It was originally founded by Arnold A. Auguste, who moved to Toronto from Trinidad and Tobago in 1970, entered a career in journalism, and began publishing Share in 1978. Share aims to provide positive news and information about the community that tend not to be covered by mainstream media outlets, as well as stories about community events. The newspaper has since grown to become the one of the largest and most influential ethnic newspapers in Canada, and is the largest one serving the Black and Caribbean community in Toronto.

Reggae Lane
1529 Eglinton Avenue West
Reggae Lane was designated in 2015 to celebrate the musical legacy of Little Jamaica as part of the Laneway Project, an initiative to transform laneways into vibrant public spaces that celebrate their neighbourhoods. This impressive 1,200-square foot mural was collaboratively designed by local youth under the mentorship of artist Adrian Hayles, in consultation with prominent reggae musicians and reggae music experts. The design is a celebration of Toronto's reggae traditions, depicting Little Jamaica resident artists, significant international reggae artists, and figures and symbols in Rastafarian culture. Many of the musicians depicted in the mural recorded and performed, or established music studios and record shops, in Little Jamaica. Also referenced is Toronto-based CFRB radio station, which was the first mainstream station in Canada to play Reggae music on a specialty program in the 1970s. At this time, it was one of the country's most popular radio stations.

Ryan Smeeton 'Together We Grow' Mural
1661 Eglinton Avenue West
Commissioned by the York-Eglinton BIA, this mural was designed and painted by Ryan Smeeton to celebrate the cultural diversity of the area. The mural depicts a hand reaching toward a large rose of Sharon (a type of hibiscus flower and a biblical symbol referenced in some reggae music). The purple flowers that appear in the mural are Lignum Vitae, the national flower of Jamaica. The use of natural imagery in the mural also speaks to the natural features of the area, including the Cedarvale Ravine and the Beltline Trail.

Toronto Public Library - Maria A. Shchuka Branch
1745 Eglinton Avenue West
This library opened as part of the Township of York Public Library Board in 1951 and was later named in honour of head librarian Maria A. Shchuka in 1997. Thanks to an extensive reconstruction in 2002, the library branch now offers many services catering to the community, including an art exhibit space, a youth hub, collections in local history and in multiple languages, a large seating capacity and equipment for people with disabilities. The library is also one of four libraries across the city to house the Rita Cox Collection, one of the most significant Black and Caribbean heritage collections in Canada. It includes over 16,000 print and audiovisual materials about the Black and Caribbean historical and cultural experience. Dr. Rita Cox is a storyteller, author and librarian who pioneered the Toronto Public Library's Black Heritage and West Indian Resource Collection. In 1997, Dr. Cox was appointed a Member of the Order of Canada for her outstanding work in storytelling and literacy.

Fairbank Memorial Park
2213 Dufferin Street
This 3.5-hectare park on Dufferin Street just south of Eglinton Avenue West features a lit ball diamond, a basketball court, a children's playground and two outdoor pools. Located onsite is the Fairbank Memorial Community Recreation Centre.

Explore Oakwood Village

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.
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 historic neighbourhood features some of the most important Black and Caribbean historical and cultural sites in Toronto. The section along Eglinton Avenue West in this area is nicknamed 'Little Jamaica' due to the high number of Jamaican businesses and organizations that call the street home, and many other spots throughout the neighbourhood proudly reflect strong Caribbean ties. Great local businesses can be found in the Oakwood Village and York-Eglinton BIAs.

Main Streets: Oakwood Avenue, Eglinton Avenue West and Vaughan Road
  1. Oakwood and St. Clair Streetcar Loop
    Oakwood Avenue and St. Clair Avenue West
    Oakwood developed as a streetcar suburb, a residential community strongly shaped by the use of streetcar lines. As the area grew and businesses opened on Eglinton Avenue, the Township of York entered an agreement with the Toronto Transit Commission (TTC) to establish the Oakwood and Rogers Road Streetcars in 1924 to meet growing ridership demands. The TTC charged an extra fare when the streetcar crossed the city limits. Today, neither streetcar line is in operation, but the loop remains and is used for the St. Clair streetcar instead.
  2. Oakwood Village Library and Arts Centre
    341 Oakwood Avenue
    Oakwood Village Public Library and Arts Centre is a community hub with educational programs for children, youth and adults, exhibition space for monthly shows by local artists, a music practice room, and an auditorium.
  3. Karen Roberts Artbox
    529 Vaughan Road
    Artist Karen Roberts has a personal connection to the Vaughan Road Academy represented on this artbox, having attended the school herself. The design uses the school's colours (red, blue and gold) and includes the school's V logo in the centre. Roberts also painted the school's mascot, various sports figures, books and paper airplanes. After serving the community for nine decades, the Vaughan Road Academy closed in 2017 due to low enrollment. Graduates of the school include actor Neve Campbell, rapper/actor Aubrey 'Drake' Graham, actor William Hutt and former Toronto Poet Laureate Anne Michaels.
  4. Laughlin Park
    420 Atlas Avenue
    A small park near Vaughan Road and Oakwood Avenue that features a children's playground.
  5. Palm Tree
    Intersection of Oakwood Avenue and Vaughan Road
    In 2010, a 4.9-metre steel palm tree was installed on the traffic island at the corner of Oakwood Avenue and Vaughan Road. Oakwood Village is home to many residents from Caribbean countries, for which the palm tree is a native species. The tree is symbolic of the roots put down by the Caribbean community.
  6. Dan Bergeron 'A Common Thread' Mural
    Intersection of Oakwood Avenue and Vaughan Road
    This new mural on the benches in the Vaughan Road and Oakwood Avenue traffic island was commissioned by the Oakwood Village BIA and Nia Centre for the Arts. It was painted by visual artist Dan Bergeron in conjunction with two emerging Black artists selected by the Nia Centre for the Arts. It depicts a quilting pattern, meant to display memories and stories from the neighbourhood.
  7. Nia Centre for the Arts
    524 Oakwood Avenue
    Nia Centre for the Arts supports local artists and showcases art from across the African Diaspora through exhibitions and festivals. The centre focuses on creating opportunities for young people and emerging artists by offering arts-based workshops, programs, events and camps. Nia is a Swahili word for purpose, and the organization is dedicated to supporting and highlighting those who have found purpose through art. The centre is currently undergoing a redevelopment process that will add a 160-seat performance theatre, co-working spaces, digital arts incubation studios, recording & visual arts studios, and community workspaces.
  8. UNISON Building Mosaic
    501 Oakwood Avenue
    A beautiful tiled mosaic along the raised landscaped edge and retaining wall of 501 Oakwood Avenue welcomes people to the neighbourhood with an expression of the word unity in several languages. The artistic creation and direction was led by Art Starts (founded in the neighbourhood) and Red Pepper Spectacle Arts. Both art organizations continue to have an impactful presence in the city. After much community advocacy, 501 Oakwood Avenue opened as a Community Health Centre in 2019.
  9. Share Magazine
    658 Vaughan Road
    This building houses the offices of Share Magazine, a weekly community newspaper that serves the Black and Caribbean community in the Greater Toronto Area (GTA). It was originally founded by Arnold A. Auguste, who moved to Toronto from Trinidad and Tobago in 1970, entered a career in journalism, and began publishing Share in 1978. Share aims to provide positive news and information about the community that tend not to be covered by mainstream media outlets, as well as stories about community events. The newspaper has since grown to become the one of the largest and most influential ethnic newspapers in Canada, and is the largest one serving the Black and Caribbean community in Toronto.
  10. Reggae Lane
    1529 Eglinton Avenue West
    Reggae Lane was designated in 2015 to celebrate the musical legacy of Little Jamaica as part of the Laneway Project, an initiative to transform laneways into vibrant public spaces that celebrate their neighbourhoods. This impressive 1,200-square foot mural was collaboratively designed by local youth under the mentorship of artist Adrian Hayles, in consultation with prominent reggae musicians and reggae music experts. The design is a celebration of Toronto's reggae traditions, depicting Little Jamaica resident artists, significant international reggae artists, and figures and symbols in Rastafarian culture. Many of the musicians depicted in the mural recorded and performed, or established music studios and record shops, in Little Jamaica. Also referenced is Toronto-based CFRB radio station, which was the first mainstream station in Canada to play Reggae music on a specialty program in the 1970s. At this time, it was one of the country's most popular radio stations.
  11. Ryan Smeeton 'Together We Grow' Mural
    1661 Eglinton Avenue West
    Commissioned by the York-Eglinton BIA, this mural was designed and painted by Ryan Smeeton to celebrate the cultural diversity of the area. The mural depicts a hand reaching toward a large rose of Sharon (a type of hibiscus flower and a biblical symbol referenced in some reggae music). The purple flowers that appear in the mural are Lignum Vitae, the national flower of Jamaica. The use of natural imagery in the mural also speaks to the natural features of the area, including the Cedarvale Ravine and the Beltline Trail.
  12. Toronto Public Library - Maria A. Shchuka Branch
    1745 Eglinton Avenue West
    This library opened as part of the Township of York Public Library Board in 1951 and was later named in honour of head librarian Maria A. Shchuka in 1997. Thanks to an extensive reconstruction in 2002, the library branch now offers many services catering to the community, including an art exhibit space, a youth hub, collections in local history and in multiple languages, a large seating capacity and equipment for people with disabilities. The library is also one of four libraries across the city to house the Rita Cox Collection, one of the most significant Black and Caribbean heritage collections in Canada. It includes over 16,000 print and audiovisual materials about the Black and Caribbean historical and cultural experience. Dr. Rita Cox is a storyteller, author and librarian who pioneered the Toronto Public Library's Black Heritage and West Indian Resource Collection. In 1997, Dr. Cox was appointed a Member of the Order of Canada for her outstanding work in storytelling and literacy.
  13. Fairbank Memorial Park
    2213 Dufferin Street
    This 3.5-hectare park on Dufferin Street just south of Eglinton Avenue West features a lit ball diamond, a basketball court, a children's playground and two outdoor pools. Located onsite is the Fairbank Memorial Community Recreation Centre.

Accessibility information: All points of interest on this stroll are visible from the street, except for Fairbank Memorial Park, which includes some staircases and unpaved paths.

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.