Ontario Highway 88

King's Highway 88, commonly referred to as Highway 88, was a provincially maintained highway located in the town of Bradford West Gwillimbury, which connected former Highway 27 in the village of Bond Head with former Highway 11 in the town of Bradford. It was established in 1938 and decommissioned in 1998, and has since been known as Simcoe County Road 88.

Highway 88 began at an intersection with what was then Highway 27, but it now known as York County Road 27, in the community of Bond Head. It proceeded eastward and encountered an interchange with Highway 400 at Exit 65. At the northwest corner of the interchange was Yogi Bear's Jellystone Park and Camp Resort. East of Highway 400, the highway entered the urban area of Bradford, where it ended at an intersection with former Highway 11, which travelled north along Yonge Street as well as east along Bridge Street.

Highway 88 was built in the 1850s and was the first plank road built in Simcoe County, which originally connected Holland Landing with Bond Head. The road was about 1 inch thick and was wide enough for a wagon. It was laid on the north or east part of the CNR rail line that still exists today. It is still in service, but the majority of traffic was transferred onto the south or western side of the tracks, when Highway 11 was constructed in the 1920s. The old section of the road can be accessed from Highway 11 but its bridge was torn down when the new bridge was constructed for Highway 11. Wooden pillars from the original bridge still are seen peeping out of the Holland River. It is an assumption that the bridge was constructed on the north side of the railway because of a shorter distance between land or better shorelines. The Road in fact probably went very close to the Bradford Train station as there was a closed road that intersected at the present day Bridge, Dissette and Holland street intersection (It was recently removed due to construction of the new GO Train parking lot). This road is almost perpendicular to the train station. The plank road had 2 main toll booths until its conversion to Highway 88. One was located at what is now 10th sideroad and Simcoe County Road 88, and the other was located near the Holland River bridge on the south side.

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