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presents

The Highways of Hamilton /

Ontario 5B, 99, and Hamilton Regional Roads 299, 399, & 99

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Highway	Duration	Start	Terminus	Length (km)
ON 5B	1938-1940	Brant County line west of Lynden	Main St. (ON 8), Dundas	21
ON 99	1940-1982	Brant County line west of Lynden	Main St. (ON 8), Dundas	21
RR 299	1982-2005?	Brant County line west of Lynden	Binkley Rd. west of Dundas	15
RR 399		Binkley Rd. west of Dundas	Main St., Dundas	6
RR 99	2005-	Brant County line west of Lynden	Cootes Dr. (RR 8), Dundas	22

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Overview

Highway 99 is an east-west road connecting downtown Dundas to Brant County, where it continues with the same number. Its entire course splits the difference between highways 5 and 403, serving as an alternate route to Paris and as a collector road passing through the communities of Copetown and Lynden along the way.

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History

Hamilton RR 99 originated in 1938 as Ontario Provincial Highway 5B, an alternate "business spur" of Highway 5 compensating for the latter road's lack of downtown connections. Highway 5B forked from its parent at Osborne Corners in Brant County and progressed in parallel for 28 kilometres (21 of them in Wentworth County), ending in downtown Dundas.

The infrastructure of Highway 5B preceded the highway itself by an order of magnitude. Its routing followed the course of Governors Road (aka Dundas Street), a military road constructed in the 1790s to link Dundas to London. Governors Road served as a survey baseline, separating Ancaster Township from Beverly and West Flamborough. A portion of Highway 5 was also built on a historical segment of this road.

Two years after being commissioned, Highway 5B was given the "promotion" of a whole number: Highway 99. This was the last new two-digit highway number assigned in Ontario.

In the 1960s and 1970s, whatever tenuous purpose Highway 99 had as a through road was sucked away by the 403 and the widening of other, more direct highways. As such, the province soon put the road on the "downloading" block. The Hamilton-Wentworth portion of Highway 99 was reclassified as a Regional Road in 1982. The Brant County portion persisted as a stub for another 15 years, then fell to the same fate.

The highway has seen the following changes:

• A: About 1959, ON 99's routing in Dundas was adjusted so that the highway ended on Governors Road instead of turning onto Ogilvie Street.
• B: By 1976, a 1.5-km segment near Copetown was realigned in order to eliminate two grade crossings with the Toronto, Hamilton, & Buffalo Railway.

• C: In 1982, the entire length of ON 99 in Hamilton-Wentworth was reclassified as a Regional Road. Around the same time, Hamilton-Wentworth adopted a code system for regional roads with a first digit keyed to the municipality. As such, ON 99 became RR 299 in Ancaster and RR 399 in Dundas.
• D: At some indeterminate point (probably either the 1997 reclassification of Highway 8 or Hamilton's 2005 restructuring of Regional Roads), the east end of Highway 99 was extended four blocks past its original terminus to end at Cootes Drive.
• E: In 2005, RR 299 and 399 reverted to the unified designation of RR 99.

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Gallery

All photos are by the author, 2022-2025:

Hamilton Regional Road 99.

This sign is posted where a 1.5-km segment of ON 99 was bypassed to eliminate railway crossings. Now the railway is abandoned, and signs encourage cyclists to use both the former grade and the former highway.

This monument stands adjacent to Dundas Valley Secondary School, and contains a plaque which addresses the history of the road as Dundas Street.

Eighteenth-century Home Secretary Henry Dundas had little to do with the road that bears his name, and in recent years more critical attention has been cast on the things he did do...namely, postpone the abolition of the slave trade. Thus, his name has fallen out of favour for commemoration, as it should be.

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Links

• Ontario Highway 99 History - The King's Highways of Ontario

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