It is divided into lines based on the concession system implemented by the British colonial government in the mid-18th century.

First Nations had long established encampments and trails on the bank of Hawkestone Creek, Ridge Road, Mount St. Louis, and throughout the Township of Oro-Medonte.

The War of 1812 drew attention to the militarily strategic region between Lake Simcoe and Georgian Bay.

To provide supplies to the excellent harbour at Penetanguishene, a road of about 35 km was surveyed c. 1813 between the two bodies of water.

After the War of 1812, Sir Peregrine Maitland, then Lieutenant-Governor of Upper Canada, offered Black veterans grants of land in what was to become the Township of Oro.

Its post office was established in the 1850s, at its peak in the late 19th century, Craighurst had four hotels, three churches, and a school house.

A thriving community of a tavern, hotel, store and the first post office was located near the lake east of the creek at Hodges' Landing.

It is thought that the first mill was established by John Williamson who subsequently built the large brick house on the North-East corner of the Ridge Road and Line No.

Many African-American refugees first settled near the water in shanties (small homes), contributing toward the name of the village.

Lucius Richard O'Brien (1832–1899), the noted oil and watercolour landscape painter was from Shanty Bay.

An extensive station complex evolved at Hawkestone, with a freight shed, stockyards and a massive water tower to supply the requirements of the steam locomotives.

The 200 acres (0.81 km2) were developed into a large recreation area and children's camp where members of the UNF and their families have spent their summers on the shores of Lake Simcoe.

The entire property was named "Sokil", which is the Ukrainian word for "Hawk" in reference to the village of Hawkestone where the community was established.

The property also hosts the St. John the Baptist Ukrainian Catholic chapel where services are conducted each Sunday throughout the summer season.

Within a few years all Blacks of any origin could acquire land in Oro Township on an equal basis as any other settler.

The Oro Black Settlement grew to about 90 families, then diminished as the settlers found steady income elsewhere (mainly on railway trains and ships on the Great Lakes).

In 2003, it was designated a Canadian national historic site, mainly due to the link the Oro settlers had to the War of 1812.

As of June 2023, this festival has been held in Oro-Medonte in consecutive years since moving from the Bowmanville Area,[23] with a show planned for August 10–13.

In 1998, the land used for the railway was acquired by city council for a shared-use recreational trail stretching from Barrie to Orillia.

Bass Lake Provincial Park and the Copeland Forest Resources Management Area are located within the township.

Its line headed northeast from a junction at Allandale (now part of Barrie), curving around the tip of Lake Simcoe and passing through the townships which would eventually become Oro-Medonte on its way to Orillia, Washago, and ultimately Gravenhurst.

Construction began in 1870, and in 1871 the company was leased to the Northern Railway of Canada and operated as a wholly owned subsidiary thereafter.

In 1917, not long before the Grand Trunk's amalgamation into Canadian National Railways (CN Rail), one of its trains derailed in front of Hawkestone station.

[31] Starting in August 2019, public transit service returned to Oro-Medonte when Simcoe County LINX Route 3 began operations, connecting Barrie to Orillia along Highway 11, with a single stop in the township at the Lake Simcoe Regional Airport in Oro Station.