The first permanent settlers in the area now known as Brookside, which is off the Prospect Road, were members of the Scottish-born Drysdale family. The son of John Drysdale and Isabella Bonner of Scotland, John Drysdale was born May 2, 1749, in Alva, Scotland. Early baptism and marriage records in Scotland for this Drysdale family are found in the counties of Stirlingshire and Clackmannanshire, in the parishes of Alloa, Alva, Dollar, and Tillcoultry.
John Drysdale brought his wife and eight children from Scotland to Nova Scotia in 1786, where four more children were born. He was granted 300 acres of Crown land, described in 1786 as being "in the rear of the Spryfield lots." Later records indicate that the grant included land on both sides of Brookside Road, from beginning to end. He called his property "Court Hill Farm." At the same time, Daniel Grant, George Parker, John Nichols and John MacDonald were granted large tracts of land adjoining the northern and western boundaries of Drysdale's grant. Most of Nichols' 400 acres and McDonald's 350 acres were located on the western side of the Prospect Road, surrounding the lakes named for these two original grantees. The grants of Drysdale, Grant, and Parker are shown on the Crown Land Grant Map as being on the eastern side of the Prospect Road.
The 1791 Poll Tax records for Spryfield show John Drysdale as a farmer with six cows. At the time, the community of Brookside did not exist, which would explain why John Drysdale was said to be living in Spryfield. That community had already acquired its name from the large farm developed between 1769 and 1780 by Captain William Spry, a military engineer and the chief engineer for Nova Scotia. By 1800, John Drysdale had acquired Grant's and Parker's land, increasing his land holdings to 800 acres. He established another farm and homestead on part of the land he purchased from Daniel Grant and called that farm "Brookside," bordering Hatchet Lake.
John Drysdale drowned December 10, 1815, "at Brookside," according to the death announcement in the Acadian Recorder. His wife, Ann Duncan, whom he married October 21, 1769, in Scotland, died in Brookside February 10, 1824. Until 1988, the gravestones of John and Ann Drysdale could still be seen on a wooded knoll overlooking Johnny's Pond on Club Road. Today the stones are no longer visible. This same cemetery was used as a burial site for at least two more generations of Drysdale descendants.
Inscribed on John Drysdale's stone was this message:
Sacred to the Memory of John Drysdale who died 10th Dec. A.D. 1815. Aged 66 Years.
Stop friend and muse beside my grave
And take this good advice from me
If you do sin and spill a stone
Apply to Christ to set you free.
In 1812, John and Ann Drysdale deeded one-half of the original 1786 Drysdale grant, including Court Hill Farm, to their eldest son John, Jr. The transaction was not finalized until 1816 following the death of his father. John Drysdale, Jr. and his descendants operated Strawhouse on Court Hill Farm, a "stopping place" for travellers on the Prospect Road for refreshments and to water and feed their horses. The address "Strawhouse" was mentioned in church records as early as 1828.
Following John Drysdale's death in 1815, his youngest daughter, Elizabeth, inherited the Drysdale homestead on Brookside Farm. In the Acadian Recorder from August 29, 1818, the marriage announcement of Elizabeth Drysdale to William Yeadon stated William was "of Harrietsfield" and Elizabeth "of Brookside." The Yeadon couple settled in Spryfield in 1833. Their eldest son, John George Yeadon, inherited his parents' land in Brookside and purchased much of the previously owned Drysdale land. Yeadon descendants continue to live on part of the original Drysdale grant.