Bradford is the primary country urban area of the Town of Bradford West Gwillimbury, Ontario, in Canada. It overlooks a farming community, known as The Holland Marsh, located on the Holland River that flows into Lake Simcoe. Within the municipal boundaries are a number of smaller communities, including: Bond Head, Dunkerron, Green Valley, Pinkerton, Fisher's Corners, Newton Robinson, Coulson and Deerhurst.
The eastern boundary of Bradford is the Holland River, named for Samuel Holland, first Surveyor General of British North America, who passed this way on an exploration from Toronto to Balsam Lake, by way of Lake Simcoe, in 1791.
For several years the Holland River and Lake Simcoe provided the only means of transportation. Holland Landing was the northern terminus of Yonge Street. The military route to Georgian Bay during the War of 1812 crossed Lake Simcoe to Kempenfelt Bay, then by the Nine Mile Portage to Willow Creek and the Nottawasaga River. The Penetanguishene Road, built between 1814 and 1815 from Kempenfelt Bay, provided an alternate route to Georgian Bay. However, early settlers also used this route to get to the frontier of Simcoe County, bypassing the areas of West Gwillimbury and Essa townships.
The first settlers to cross the Holland River, arriving in the fall of 1819, were three Irishmen: James Wallace, Lewis Algeo and Robert Armstrong. This was about the same time as the Auld Kirk Scotch Settlement was established. However, the pioneers of West Gwillimbury were mostly Protestants from Northern Ireland.
The new settlers sent a petition to the province of Upper Canada early in 1824, stating they were separated from the settlements of Yonge Street, by an impassable swamp. On January 24 the Legislative Assembly of Upper Canada made a grant for the first main road in West Gwillimbury (4 Geo. 1V., chap 29). The contract for the first corduroy road across the Holland Marsh was completed by Robert Armstrong and his sons in the fall of 1825. Connecting with other contactors sections and the previously constructed road from Kempenfelt Bay, the road became known as Penetanguishene Road. It later became part of Yonge Street, and is now Simcoe County Road 4.