The region's economy of the 1800's revolved around agriculture (in the south) and the lumber industry. Many of the tall pine trees (some as tall as two hundred feet) that grew in the area were cut down and used as masts for British ships. Logs crowded the rivers floating down to feed saw mills.
By the 1820s, stage coaches regularly travelled the Yonge Street route, and by the late 1830s 12 miles of the route was macadamized (made of layers of gravel, for better drainage). By 1830, British surveyor laid out a road between Oakville and Owen Sound, to connect Lake Ontario to Lake Huron. For two decades of roadbuilding, plank roads proved more cost-effective than macadmized roads, and helped develop the interior of the province. In the 1820s Admiral Henry Wolsey Bayfield was commissioned to survey and map out Lake Huron as well as Georgian Bay.
The War of 1812 taught the British that the Great Lakes were vulnerable to American attack, including their forts at what are now Detroit and Sault Ste Marie, so in 1820, the first plans were proposed for a Trent Canal, and in 1825 rough roads were built into the area. When the Crown failed to advance the canal, settlers in the area went ahead on their own, offering land grants to workers who came over from England to help build the canal. By 1830 the lumbermen, working to get the area's forests to market, also got onside with a Trent canal.
The Muskoka Road connected Severn Bridge (north of Orillia) to North Bay. This road was begun in 1859 and coimpleted in 1875, and today is the route of Highway 11 To encourage settlement in the Parry Sound area, the Rosseau-Nipissing Road was authorized by the government in 1864, and construction began in 1866. It connected Rosseau, South River and Nipising, and by 1873 was open for winter traffic and by 1875 was usable by wheeled vehicles.
The promise of work at the sawmills in conjunction with the Free Grants & Homestead Act of 1868 offered 100 to 200 acres of land to prospective farmers, on the condition they stay and work the land for at least five years
In 1853, the Ontario Simcoe Huron Railway (later the Northern Railway) connected the City of York (now Toronto) to the southwest corner of Kempenfelt Bay, at Allandale. The line was extended to Barrie in 1865. A railway company steamer carried passengers to Orillia and Muskoka. A railway was also built between Gravenhurst and Callander in 1886.
Barrie was officially incorporated as a Town in 1871, and the first mayor of Barrie was Robert Simpson.