Stephenson Township was first shown on the Crown Lands map in 1861. Robert Gilmour surveyed most of the township that same year. Ten years later lots 1 to 20 in Con. 12, 13 and 14 were also surveyed. Stephenson Township contains 42,973 acres of land and 3,262 acres of water. Mr. Gilmour reported land "generally of a good quality south of the Seventh Concession". The northwest part of the township along the shores of Skeleton Lake is very rugged with granite ridges and steeply cut valleys.
The survey of the Muskoka Road north of Bracebridge was done in 1860 and the road was built from Bracebridge to the north boundary of Stephenson Township in 1863. The settlers came as the road opened. The continuation of the road to Huntsville was not complete until 1871. over the years, roads were a continual source of aggravation and the Colonization Land Commission received many petitions pleading for more roads and improvements to existing roads.
With the arrival of large steamships on the lakes, the transportation dilemma was relieved to some degree. A settler travelling from Toronto to Stephenson Township in 1869 would take the train to Belle Ewart on Lake Simcoe, a steamer to Orillia and Washago. The journey from Washago to Gravenhurst by stage was followed by a steamer to Bracebridge and then by stage to Utterson from whence one proceeded on foot to his destination. By the end of 1867 there were enough inhabitants for Stephenson to have some measure of local government through the adjacent united townships of Draper, McCauley and Ryde. In 1868 this council appointed seven "pathmasters" or road overseers in Stephenson Township. In 1871 the township formed its own council.
By 1879 almost all the land was taken up. Settlement duties included residing on the land, clearing and cultivating at least 15 acres within five years and building a house. Locations could be taken up by either sex, eighteen years of age or over. Many a spinster achieved an instant dowry under these terms! There were families that acquired as many as 500 or more acres in the names of their sons and daughters. The Crown reserved the minerals and also the right to all pine trees on the lots; any remaining pine trees passed to the settler when he or she obtained full title at the end of five years.
Three villages developed in Stephenson Township. Utterson and Allanville on the Muskoka Road, and Port Sydney at the end of Mary Lake.
Utterson, for a short period in the very early years (cl868), was called Brunel Junction when the secondary colonization road to Brunel Township was surveyed from this location to the east. In 1879 there was a store, blacksmith shop, a large hotel "well conducted by Mr. Collins", a well-built Connexion Methodist Church with stained glass windows, a town hall three stages and mail delivery daily to Bracebridge.
Port Sydney, in the Guide Book and Atlas of Muskoka and Parry Sound 1879, was described as a "charmingly situated" village on Mary's Lake. Tourists were attracted to the well-kept hotel. Boat excursions along the picturesque shores of Mary Lake were a feature attraction. The village at that time boasted a public school, several good private residences, a large public hall in which amateur dramatic performances were given with great effect and got up regardless of expense", a grist mill, oatmeal mill, saw mill, some good stores and the Anglican Church, "a gothic edifice, furnished with stained glass windows, in lasting memory of Rev. Cooper, through whose exertions mainly the church was built." The guidebook said Port Sydney was reached from Huntsville in the summer by the steamer Northern and that it enjoyed a tri-weekly mail from Bracebridge, "with a daily stage in the summer".
In 1885 the railway reached Bracebridge and in 1886 it was extended to Utterson, in Stephenson Township, and on to Huntsville. Having the railway bypass their village was a blow to Port Sydney residents who'd hoped to see the town develop as a major distribution centre. The stage route to Utterson became the focus of Port Sydney until fifty years later when the automobile became commonplace releasing residents and tourists alike from their dependence on steamboats and railways.
From the earliest years, people came with great anticipation for a bright new future, whether it be to farm or work in the bush, or to provide a service to a newly developing community. Many left for the west, some to elsewhere in Ontario. Yet now, 125 years since the first settler came, there are still many descendants of these families living in Stephenson Township.