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Woodbine Avenue is a north–south arterial road consisting of two sections in Toronto and York Region in Ontario, Canada.
The northern section runs from Steeles Avenue at the Toronto-Markham border and extends to the shore of Lake Simcoe, ending at Lake Drive in Georgina. York Region designates this section as York Regional Road 8. The map identifies current and planned arterial designated roads in York Region, including Woodbine. Woodbine Avenue runs parallel to Highway 404, with the highway's northern terminus branching off it just south of Ravenshoe Road in East Gwillimbury. Woodbine in York Region is six lanes wide from Steeles Avenue to Highway 7, and four lanes wide from Highway 7 to north of Elgin Mills Road, passing through the Markham neighbourhoods of Buttonville, Cachet, and Cathedraltown, with a bypass around the preserved former rural community of Victoria Square. North of Elgin Mills, Woodbine narrows to a two-lane rural road.
There is also a short former third section immediately to the north of the Toronto section; cut off by the Taylor-Massey Creek, in the Parkview Hills neighbourhood, which is today named Woodbine Heights Boulevard. It runs for four blocks and ends at the East Don Valley of the Don River.
Union Street in Gormley is a former alignment of Woodbine at Stouffville Road.
It was named for Woodbine Racetrack, later known as Greenwood Raceway. Beyond Lawrence Avenue and especially south of Eglinton Avenue the road allowance was not feasible for a roadway due to the deep valley along the Don River. It is also believed that former racetrack-owner William J. (Jiggs) Howell (along with either Raymond Pardee or Dennis Pard) operated a tavern at then 88 Yonge Street (west side of Yonge north of King Street near the Fairweather Building c. 1918) called "The Woodbine House" or "The Woodbine", which was re-used by Howell for his horse track.
Originally, Woodbine Avenue's southern terminus was at the namesake Woodbine Beach on Ashbridge's Bay just south of Kew Beach Avenue which is two blocks south of Queen Street, but was rechannelled to curve west into the eastern end of the then-new Lake Shore Boulevard in the 1950s.
In Toronto, portions of unopened and open road allowances for Woodbine Avenue north of Eglinton Avenue to Sheppard Avenue were removed when the Don Valley Parkway was constructed in the 1960s, with the terminus of Don Valley Parkway defaulting to Woodbine Avenue. The last section of Woodbine in Metropolitan Toronto between Sheppard Avenue and Steeles Avenue was lost when the provincial extension of the Don Valley Parkway, Highway 404, was built over it during the 1970s. Woodbine was retained north of Steeles through York Region by swinging the route of Highway 404 to the west, with the Parclo A4 interchange with Steeles including a Y-junction to accommodate traffic to and from Woodbine towards the south. Victoria Park Avenue, a major north–south arterial extending north from the City of Toronto, terminates shortly after the intersection with Steeles, with Woodbine absorbing most of this traffic.
In the early 2000s, new housing development necessitated the widening of Woodbine Avenue north of Major Mackenzie Drive to cope with increased traffic levels. However, due to residences and heritage properties in the community of Victoria Square, including a church and 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 alignment, which was initially known as Woodbine Avenue By-Pass, opened on November 15, 2010. Woodbine Avenue Bypass to Open in Town of Markham The bypassed section of Woodbine Avenue was renamed Victoria Square Boulevard to reflect the location of the road within the area of Victoria Square and transferred to the jurisdiction of the city of Markham. However, the bypass retained the Woodbine Avenue By-Pass name even after the renaming of the bypassed segment until November 2015, when it was finally decided to redesignate it as part of Woodbine Avenue proper. The former alignment, Victoria Square Boulevard, intersects Woodbine at both ends.
In 2017, the City of Toronto installed Cycle Tracks (protected bike lanes) to Woodbine Ave spanning from O'Connor Dr to Queen St E.
The privately operated Hollinger route was taken over by the TTC in 1954 and retained route name. The opening of Woodbine subway station in 1966 changed transit patterns, as many residents now needed to get all the way north to Danforth.
Today Woodbine is served by five different routes and two operators. The northern part of the route, from Danforth to O'Connor is served by the TTC 91 Woodbine and 93 Parkview Hills bus routes. South of Danforth is served by TTC 92 Woodbine South bus route.
In Markham the road is served by the 24 Woodbine YRT route. The far north of the road, through the town of Keswick is served by YRT 51 Keswick Local.
| Woodbine Beach | Lake Ontario | Part of The Beaches Park (established after the sale of Ashbridge Estate in the 1920s) and is maintained by Toronto Parks, Forestry and Recreation Division | |
| Greenwood Raceway | Lake Shore Blvd | Racetrack (1874-1994) demolished in the late 1990s and now home to residential development | |
| St. John's Cemetery Norway | Kingston Road | Church opened 1853 | |
| St. John the Baptist, Norway Anglican Church | Kingston Road | Opened 1853 along with St. John's Cemetery Norway | |
| Woodbine subway station | Danforth Avenue | Station on Bloor–Danforth line opened 1966 | |
| Toronto Chinese Mennonite Church | North of Danforth Avenue | Formerly Rogers Memorial Presbyterian 1922-2000 |
| Cathedral of the Transfiguration | Major Mackenzie Drive East | ||
| Fletcher's Fields | 19th Avenue | Rugby Stadium/Field and home to Toronto Rebellion of the Rugby Canada Super League | |
| Preston Lake | Bloomington Road East | Village settled in 1802 next to Kettle lake, private access only (700 members of Landford Preston Lake Limited and Preston Lake Country Club) |
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