The history of Richmond Hill began when the First Nations came and settled in the area. With the Toronto Purchase, the city gradually expanded with new greenhouse industries and improved transportation infrastructure.

First Nations The first humans to come to the area were probably Paleo-Indians between 9000 and 7000 BCE.; see also Archaeological Services, Inc., "Town of Richmond Hill Official Plan: Archaeological and First Nations Policy Study ," October 2009; "The Stage 4 Salvage Excavation of the Orion Site ," Dec. 2008. The first archaeological evidence of their presence found was a single scraper found at the Mortson site near Leslie Street and Elgin Mills Road. A few more artifacts were later found east of Lake Wilcox at the Esox site and as of 1988, fourteen sites in Richmond Hill have produced Paleo-Indian artifacts. The people in southern Ontario at this time were organized in nomadic bands, and would have migrated through the area, establishing camps then moving on. The Silver Stream site, which is located on a tributary of the Rouge River west of Leslie Street, between Elgin Mills Road and Major Mackenzie Drive, has yielded 27 artifacts that come from peoples of the Paleo-Indian cultures, one of which was dated to 1800 BCE.

Eventually, the regional cultural transitioned from Paleo-Indian to Archaic, and then from Archaic to Early Iroquoian. The oldest known Iroquoian site in Richmond Hill is the Wilcox Lake Site, on the east side of Lake Wilcox, which has been dated to 1300 CE. The site covers 12,000 square metres. Human habitation of the area became permanent settlements around this time, where it had previously been nomadic. Well studied is the Boyle-Atkinson Site, a Late Iroquoian settlement southwest of the intersection of Yonge Street and Major Mackenzie Drive. The location was first identified as the remains of an old settlement by David Boyle in the late 1860s. The site was occupied from about 1450 to 1500 CE and was a large village in the area, with at least nine longhouses identified as well as two other buildings. Several other sites in Richmond Hill are known to be from Iroquoian peoples who lived in the area between 1300 and 1550 CE, including the McGaw, Murphy-Goulding, Orion, Reuben Heise and Watford sites. The arrangement of the sites suggest they represent a single community periodically relocating. Around 1550 tensions between the Iroquois of southern Ontario and the Five Nations Iroquois in New York led to their emigration en masse to the Huron Confederacy between Lake Simcoe and Georgian Bay, and the archaeological evidence suggests the Iroquois inhabitants of Richmond Hill left the area about that time.

The area was uninhabited for at least 100 years after the exodus of the Iroquois. Sometime in the late 17th or early 18th century, the Mississauga Indians moved into the area from the north. The Mississaugas had a nomadic lifestyle, and moved seasonally across much of what is now York Region and the Golden Horseshoe.

Toronto purchase and early settlement

The Toronto Purchase took place on September 23, 1787, between the British and the Mississauga Indians. The purchase was understood by David Smith, the Surveyor General for Upper Canada to include the Richmond Hill area. The Mississauga Indians had a different understanding of the northern limit of the purchase. Conflicts arose between the Europeans that began to move into the area and the Mississaugas. The area was first surveyed by Augustus Jones for Lieutenant-Governor John Graves Simcoe in 1794 while he was constructing Yonge Street. By 1797, the Mississaugas in the area had left for the regions of Niagara and Peterborough. A meeting between British officials and Mississauga chiefs in 1805 clarified the northern border placing Richmond Hill within the land of the Toronto Purchase. At this time, the land that later became Richmond Hill was divided between Vaughan township west of Yonge Street, and Markham township east of Yonge Street.

The first European settlers to arrive in Richmond Hill were Balsar and Katharine Munshaw, accompanied by their children: John, George, Jacob, Betsy and Polly, who arrived in Richmond Hill in the spring of 1794 from Pennsylvania. They cleared a plot of land in the Elgin Mills area (then still in Markham). That summer, their sixth child, a daughter named Susan Munshaw was born. She was the first European settler born in Richmond Hill, and the oldest recorded birth. The Munshaws soon found their location too isolated from other European settlers in the area, and resettled themselves on the south-west corner of Yonge Street and Highway 7, outside of Richmond Hill (in what is the Vaughan section of Thornhill).

In 1794, the present-day Bayview Avenue and Leslie Street were also laid out and planned, and sometime in the late part of 1794 the first settlers arrived in the area. Some two hundred people led by William Berczy arrived in Markham township from western New York and Pennsylvania after being promised land grants in Markham township in exchange for working on the construction of Yonge Street, in an arrangement Berczy made with the Executive Council of Upper Canada. The surveyor assigned to the area known as Markham township was Abraham Iredell, he was able to begin settling the followers of Berczy in Markham township by November 1794. Some were settled in the second and third concessions which today are part of Richmond Hill, others were settled further east in what would become Markham. Arriving in November, the settlers spent the first winter in miserable conditions, unable to grow any crops before winter. Some supplies were made available to them by the German Land Company of New York and the government of Upper Canada. Crop failures occurred with these settlers in 1795 and 1796, and soon a third of them had left their homesteads. In 1796 it was decided that deeds for these lots would not be issued to Berczy and his associates, as they were not naturalised citizens of the United Kingdom. The German Land Company of New York stopped supporting the settlers and Berczy left, but some settlers stayed on. The presence of these German speaking settlers in Markham township would attract other German speakers in the coming years.

The next settler to try his hand at the Vaughan township part of Richmond Hill was John C. Stooks, who arrived there with his wife in June 1797. Arriving in York, the Stooks travelled north along Yonge Street and settled on lot 47 of Vaughan township, on the west side of Yonge Street one lot north of Major Mackenzie Drive. The Stooks, too, found the life a difficult one, they cleared little land and built only a modest house before abandoning the area and moving on. Stooks would serve in the York Militia during the War of 1812, then acquiring land in Nottawasaga Township and later moved to King Township.

The first settlers to come to Richmond Hill and remain there for more than a few years were Hugh and Ann Shaw who arrived in 1798 and occupied lot 46 on the northeast corner of Yonge Street and Major Mackenzie Drive. Other lots along Yonge Street quickly became occupied, with Thomas Kinnear in lot 48, William Jarvis in lot 49 and William McLennan in lot 50 east of Yonge Street. West of Yonge street, Abner Miles occupied lot 46 and Samuel Heron on lot 49. The first settlers of the area received land grants either by the Lieutenant Governor directly or by the Executive Council of Upper Canada, typically either as a reward for previous military service to the British Empire or because they were believed to be good settlers who would contribute substantially to the development.

Lieutenant Governor John Graves Simcoe developed a special plan for the settlement of Yonge Street that excluded the usual crown reserves and clergy reserves and opened every lot along Yonge Street to permanent settlement. Other concessions in Vaughan township and Markham township allocated two of every seven lots as reserves, with one for the crown and one for the Protestant clergy. Simcoe felt it was important to develop Yonge Street as a route to Georgian Bay and the upper Great Lakes, which motivate his Yonge Street plan. Each lot was open to any settler who arrived on the land and developed it to meet certain conditions. In 1794, this condition was merely that a dwelling be erected on the plot of land and it be occupied within one year. In 1798, this condition was increased so that the dwelling had to measure at least by , and no less than of land had to be cleared and fenced. Such settlers were additionally responsible for clearing their part of the Yonge Street right of way of brush. This plan proved ineffective, and lots on Yonge Street were slower to become occupied than the other lots in Vaughan township. In 1802, thirteen of Yonge Street's 25 concessions in Vaughan township were occupied, while in the next concession twenty of the twenty-five lots were occupied by that time. Development of Richmond Hill was also slow because of the lack of mills in the area.

Starting with forty-one people in 1798, French royalist settlers led by Joseph-Geneviève Comte de Puisaye, began settling along Yonge Street from today's Elgin Mills Road north to Stouffville Road. The Legislative Council of Upper Canada had some misgivings about the suitability of these settlers for the land, but the French Royalist officers who had left France after the French Revolution were given land grants comparable to those given to United Empire Loyalists who had come to Upper Canada after the American Revolution. Their community was named Windham to honour William Windham the British official who had arranged for their settlement there, but was locally referred to as Puisaye Town. De Puisaye and Augustus Jones went to survey the area in December 1798 while the other settlers remained in York, supported by government supplies. The de Puisaye settlers soon went north, and by January 1799 trees were being cleared from lots. On February 14, 1799, eighteen log cabins had been constructed, but not finished. The settlers' work slowed as 1799 dragged on, and individuals began leaving Windham for more developed areas: Montreal, New York and even Europe. De Puisaye soon moved to the Niagara region, although he continued to work for the betterment of Puisaye Town. Of all the settlers who came to Markham township with de Puisaye, only Le Chevalier Michel Saigeon seems to have stayed and prospered. Laurent Quetton St. George, a settler who arrived in Windham in 1799 also stayed in Upper Canada and prospered, making a career as a fur trader.

Miles' Hill: The nineteenth century dawns