The middle section in Toronto begins, under the name Woodbine Heights Drive, across the Massey Taylor Creek, in the Parkview Heights neighbourhood. Following the southern alignment of Woodbine, it continues for four blocks and ends at the East Don Valley. Had the alignment of the O'Connor Bridge been north–south instead of southwest–northeast, this section would have been joined with the southern segment.
Woodbine was a single lane paved concession road east of Yonge Street from Steeles Avenue to York Mills Road and an open allowance southwards to Lawrence Avenue East. It was named for Woodbine Racetrack, later as Greenwood Raceway. It is also believe that former track owner William J. Howell operated a tavern at then 88 Yonge Street called The Woodbine House which was re-used by Howell for his horse track. In Toronto, the portion of Woodbine Avenue north of Eglinton Avenue to Highway 401 was removed when the Don Valley Parkway was constructed in the 1960s. Another section from Highway 401 to Steeles Avenue was lost when Highway 404 was built over it during the 1970s, although the Parclo A4 interchange with Steeles included a Y-junction modification to accommodate traffic from York Regional Road 8. Victoria Park Avenue, a major north–south arterial in the City of Toronto, terminates shortly after the intersection with Steeles, so York Regional Road 8 absorbs most of this traffic. As York Regional Road 8, Woodbine Avenue is six lanes wide from Steeles Avenue to Highway 7, and four lanes wide between Highway 7 and Major Mackenzie Drive, and there is a centre turning lane. North of Major Mackenzie Drive, Woodbine narrows to a two-lane rural road, though with occasional left-turn lane. Recent housing developments since the early 2000s have necessitated the widening of Woodbine to cope with increased traffic levels. However, due to existing properties around Victoria Square including a cemetery, a new four-lane section of Woodbine was constructed on a new alignment which included a new intersection with Elgin Mills Road. The new segment which was initially known as Woodbine Avenue By-Pass opened on November 15, 2010. Woodbine Avenue By-Pass cuts through the new home development area known as Cathedraltown. It was requested by the city ofMarkham that the by-passed Woodbine Avenue would be renamed Victoria Square Boulevard to reflect the geographical location of the road—within the area of Victoria Square. However, the Woodbine Avenue By-Pass will retain the By-Pass even after the renaming of the by-passed Woodbine Avenue. Victoria Square Boulevard was transferred to the jurisdiction of the city of Markham and no longer serves as a regional road with Woodbine Avenue By-Pass now as a regional road instead. The former section is now a local road ending with cul-de-sac on either end. In 2017, the City of Toronto installed Cycle Tracks to Woodbine Ave spanning from O'Connor Dr to Queen St E.
Public Transit
Woodbine south of Danforth is served by the 92 Woodbine South bus route. Transit service along Woodbine only began in the 1950s, before then it was assumed that anyone along Woodbine could walk to one of the many east–west streetcar lines. The opening of Woodbine subway station in 1966 changed transit patterns, as many residents now needed to get all the way north to Danforth. The northern part of the route, from Danforth to O'Connor is served by the 91 Woodbine and 93 Parkview Hills bus routes. The portion of Woodbine in Markham is served by the 24 Woodbine YRT route. The far north of the road, through the town of Keswick is served by York Region Transit's 51 Keswick Local.
Landmarks
Landmarks and notable sites along Woodbine from south to north:
Southern section
Northern section
Other
On Christmas Eve, in 2001, the Woodbine Building Supply fire occurred. The store was located at the intersection of Danforth and Woodbine. It was one of the biggest fires in Toronto's history, as 170 firefighters were required to bring the six-alarm blaze under control. The building was less than 50 metres from residences in the neighborhood and more than 50 families had to evacuate their homes on Christmas morning. One person was killed and another was severely disfigured. Police and insurance quickly suspected arson and several people have been convicted.
Distinction from Woodbine Racetrack
is in Etobicoke, and not anywhere close to Woodbine Avenue. Greenwood Race Track used to be located at the south end of Woodbine Avenue until it was demolished in 1994. Greenwood Race Track was the original Woodbine Racetrack until the construction of the current Woodbine Racetrack in 1956. The name was then transferred to the new facility. Known as "Old Woodbine Race Track" for several years, the facility changed its name to Greenwood Race Track after nearby Greenwood Avenue.
