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Road in Toronto, Ontario, Canada

Sheppard Avenue is an east–west principal arterial road in Toronto, Ontario, Canada. The street has two distinct branches near its eastern end, with the original route being a collector road leading to Pickering via a turnoff, and the main route following a later built roadway which runs south to Kingston Road. To avoid name duplication, the Toronto portion of the northern branch was renamed Twyn Rivers Drive. The section of the street entirely in Toronto is (34.2 km) in length, while the Pickering section and Twyn Rivers Dr. is (5.4 km) long.

East of Yonge Street, Sheppard travels east through North York to Highway 404. Historically, it continued straight to Victoria Park Avenue at the Scarborough border, where drivers then turned south to meet up with the Sheppard section through Scarborough. However, a new section called the Lansing Cutoff was constructed joining the two disconnected pieces. The orphaned section of Sheppard between the 404 and Victoria Park was renamed Old Sheppard Avenue. Sheppard continues straight east through Scarborough until just east of Meadowvale Road, where the Rouge River valley presents steep grades , and so Sheppard curves southwards to meet Kingston Road just north of Highway 401. At that junction, it also meets Port Union Road, which heads south into the Port Union neighbourhood. However, the street originally continued straight east into the Rouge valley, but that section was renamed Twyn Rivers Drive after the connection to Port Union Rd was made in the early 1950s, though Twyn Rivers becomes Sheppard again (thus officially giving the street its two branches) at Altona Road just east of the Toronto Pickering limits in Durham Region. It continues farther east as a collector road until it ends at Fairport Road just north of Kingston Road. This routing parallels the alignment for Highway 401 and serves as an alternative if the highway is closed or congested.

West of Yonge Street, Sheppard travels west across the Sheppard Avenue Bridge over the Don and past Bathurst Street and Wilson Heights Boulevard. Further west, the road allowance became blocked in 1939 by the appropriation of land for a De Havilland aircraft plant and, after World War II, Canadian Forces Base Downsview. A crescent shaped section of road was finally constructed along the northern edge of the now former base in the 1970s, connecting Sheppard at Wilson Heights to Keele Street. Today, Sheppard also intersects Allen Road on this section, but the intersecting portion of Allen Road was not constructed until 1982. Sheppard Avenue continues still further west to Weston Road and ends there due to the wide valley at the confluence of the two branches of the Humber River, preventing it from continuing further west.