Home of the Hon. James Crooks, West Flamborough, Ontario, ca 1880
The area has a long history of human occupation. There is evidence in the immediate area of Paleo-Indian occupation. Later, the area was inhabited by the aboriginal people known variously as the Neutral or Attawandaron until they were annihilated by the Iroquois nations from what is now New York State. The first recorded visit to the area by Europeans was on September 24, 1669, when the French explorers La Salle and Joliet met near Tinawatawa, now Westover. When New France was conquered by the British in 1763, the territory became part of the British Empire.
After the American Revolution in 1783 and the creation of Upper Canada, land at the western end of Lake Ontario was surveyed and organized into townships, which included East Flamborough, West Flamborough and Beverly. Governor's Road (also known as Queen's Highway 99 and later Regional Roads 399 and 299) was built on the border with neighbouring Ancaster Township in 1794–95, linking York (later Toronto) and London.
The three townships and Village of Waterdown were founding constituents of Wentworth County in 1816. The Village of Waterdown was created in 1879 from that part of East Flamborough above the Niagara Escarpment and within approximately a kilometre of King's Highway No. 5 (Dundas Street). The Town of Dundas was created from parts of West Flamborough and Ancaster Townships.
Lionel Beaumaurice "Leo" Clarke was born near Waterdown in 1892, and his family left for Winnipeg, Manitoba, in 1903. During the First World War, he enlisted in the Canadian Expeditionary Force and fought in France. On September 9, 1916, during the Battle of Somme, Corporal L.B. Clarke single-handedly repulsed a German attack. Unfortunately, he was killed in combat on October 19, 1916 before he could receive his Victoria Cross.