Road Side and Oat Garden

Unfortunately there are no surviving road maps of the Caplin Bay area for the 1800s. However, from information gleaned from some old documents, it would appear that the road from The Cross towards Ferryland may have ran eastward, towards the area today referred to as The Point. Turning southward near this location, it ascended The Hill and continued inland to avoid the Deep Cove Valley. The road eventually turned eastward again, crossing Deep Cove River, and continued on towards Ferryland. It appears that the area along the road leading from The Cross, before it turned southward, was referred to as the Road Side. North of this road was another area sometimes referred to as the Oat Garden. A number of families are recorded in the voters list as living in this area.

It appears that the property on the north and south side of the road, immediately east of The Cross, was owned by the Sweetlands. In 1817, some of the property on the south side of the road was purchased by the Sweetlands from Patrick Clancy. The deed states that the western boundary was a road leading from the Old Woman's Pond to the existing fishing room of the Sweetlands. This old deed also shows that in 1830, Patrick Clancy was actually still living on part of that land and renting it from Benjamin Sweetland. However, another deed in 1836 makes reference to one boundary of a property being Patrick Clancy's Plantation, possibly indicating that Patrick may have regained possession of some of his original property when the Sweetlands left Caplin Bay. In the voters lists, the Clancys (Patrick, and later John Clancy), are usually referred to as living at the Road Side.

In the 1836 deed mentioned above, Matthew Morry sold property at Caplin Bay, which had formerly been known as the Gregory Plantation. It is not known when the Gregorys left this property, but there is indication that Peter, possibly a son of James Gregory, later settled north west of Caplin Bay, on the road to Cape Broyle. However, the property in 1836 was occupied by Matthew Whelan and his family. The land description in the deed appears to place this homestead at the junction of what is today Route 10 (towards Ferryland) and the road to The Point. It is likely that this was the dwelling, last owned by Thomas Whelan, that was torn down in the 1950s. Adjacent to this property, on the north west side of the road was the Oat Garden. In the voters lists, Matthew Whelan (Phelan, etc.) is shown living at the Road Side or the Oat Garden. Sometime before the late 1860s, it appears that a new section of the road was extended from the foot of the Old Woman's Pond, crossing the Sweetland property, to connect with the road to Ferryland. Matthew Whelan Jr. built a house, on the south side of this road. This house was used by several generations of the Whelan family, until it was torn down in the 1990s.

Another family who settled in the Road Side area was the second generation of the Johnston family. William Johnston married Ellen Rossiter in the mid 1840s. It is not known where the original homestead was, but the Johnston house, that is still occupied today, probably dates back to the William's son, Peter Johnson, who was married in 1889. This house was built on the "new" road leading from the Old Woman's Pond. The property is adjacent to what was described in old documents as the Clancy Plantation, and opposite the area known as the Oat Garden.

John Rossiter is also shown in the voters list as living at Road Side. Again it is hard to determine the location of the original homestead, but it was probably on, or near, the property where his great grandson Patrick Rossiter built the house that exists today. Although there is no clear indication, it appears that William Rossiter who married Bridget Whelan, (daughter of Matthew and Margaret Whelan?) may also have lived in the same area.

In the 1867 Bill of Sale for the Sweetland property, it is mentioned that part of that property had a boundary with the Ryan and Flannigan plantation. Although the votes lists up to 1859 do not identify families of either surname in this area, a Ryan family did eventually settle in that area. Michael Ryan, who was born in 1853, had a house and property in the general area of the boundary mentioned in the sale of the Sweetland property. This house, which eventually became the home of his son, Michael, is still in use today.