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Middle Crossroad in the township of Oro-Medonte in Simcoe County, Ontariomarker was a pioneer colonization road and now carries the traffic of Highway 11 north of Barriemarker, between the Crown Hill interchange and the City of Orilliamarker.

Middle Crossroad through the former township of Oro was surveyed by Neil McLean, in 1843. McLean's report, submitted to the Simcoe County District Council, in August of that year, a By-Law was passed and the road was established. Much of the route starting from the Penetanguishene Road (built 1814-1815), had been an Indian trail through the forest, and its establishment shows the necessity the pioneers were under to select for their forest roads, the same courses which the Indians had selected, neither of them having the means of running roads though the woods, over swamps, hills and other obstructions, as we do to-day.

The Upper Crossroad through Oro township, was surveyed in 1844 by James Tudhope, from the Penetanguishene Road to Orillia. Also known as the Orillia Road and currently as the Old Barrie Road (Simcoe County Road 11). Early communities on this road include: Whites Corners (Dalston), Richardson's Corners (Edgar) and Rugby.

As early as 1842, the need for a road between Barrie and Orillia, had been a subject of debate by the Legislative Assembly of the Province of Canada. About December, 1846, Casimir Gzowski, then working on the Whitby and Sturgeon Bay Road near Orillia, examined different lines for a direct road between Barrie and Orillia. Following Gzowski's preliminary inspection, the Ridge Road, surveyed by James Tudhope and County surveyor Henry Creswicke Sr., was finally opened in 1848.

The Ridge Road (now part of Simcoe County Road 20), begins at Shanty Bay and is named for a ridge running along the shore of Lake Simcoemarker, for some distance from the head of Kempenfelt Baymarker. That portion of road to the west, known as Shanty Bay Road, was built prior to 1848. Early settlers in this region had noted the existence of a trail along the ridge, between Barrie and Oro Station, as early as 1815. It was thought to have been an old Indian trail, as there were traces of a few Indian villages along the ridge, and with the exception of a few minor streams, no swamps to cut off travel.

The Ridge Road, having been laid out after both the Middle Crossroad and the Upper Crossroad, the latter became the Stagecoach route, or main road for travel between Barrie and Orillia. Following the opening (to Orillia), of the Muskoka branch of the Northern Railway of Canada in 1870, stage lines had to compete with the railway for business, of these three routes the Ridge Road became the main road of travel through Oro.

On October 20, 1919, Ernest Charles Drury of Crown Hill, was elected Premier of Ontario, in forming his Cabinet, he created the Department Public Works and Highways, which he promoted Frank Campbell Biggs, of Wentworth County, as Minister. Biggs was a road enthusiast, who had done a great deal for good roads in his own locality. It was under Mr. Biggs direction, that Highway 11 came into being.

The new highway was originally planned as a trunk road to connect the communities of Southern Ontario to those of Northern Ontario, as one continuous route from Toronto to North Baymarker. For that portion of the route between Barrie and Orillia, there were three choices, the Ridge Road, the Middle Crossroad and the Upper Crossroad, each had its own set of advocates, and each formed its own committee to put forward its case. Since one of the proposed routes would pass Drury's farm, he refused to take part in the matter, but promised to have the Minister up there, to hear their claims.

Briggs had his faults, his manner was abrupt and dictatorial, and he made enemies needlessly. One summer day he went over the three routes with his chief engineer, and met the three delegations the next morning at the Pavilion in Barrie's Queen's Park. He listened to their presentations with an obvious air of boredom, and then said, "Well, Gentlemen, I may as well tell you that I have already decided on the route. And when the road is built, I'm sure you will all agree that it has been put in the right place." He made no explanation, and didn't even tell them which route he had chosen.

References

A History of Simcoe County, (1909) by Andrew F Hunter 1863-1940. Volume 1

Farmer Premier, Memoirs of the Honourable E. C. Drury, by Ernest Charles Drury (1966)


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