The Iroquois Seneca people had established river-side villages such as Ganatsekwyagon on Rouge and Teiaiagon on Humber in what is now the Greater Toronto Area.

However, the Duffins Creek was not as attractive for building a settlement, because of low navigability and the existence of a sand bar at its mouth which prevented boats from entering it.

[9] Mike Duffin (died c. 1791[10]), a fur trader of Irish descent, was the earliest European to settle in the area that later came to be known as Pickering Village.

Past Years in Pickering, a 1911 book by William R. Wood, describes him as a "King's County Irishman" who had come from "the Green Isle".

Duffins cleared a few acres of forest land, but survived mainly by fishing, hunting (fowl and deer), and eating tubers.

A Methodist minister, who traveled across Ontario, used to meet Duffin when passing through the area, and found his dead body one day.

[11] Major John Smith of 5th Regiment of Foot, who had served the commanding officer at Detroit, became the first person to receive a land patent in the region.

[16] The writings of Timothy Rogers' son Wing suggest that the area was remained densely forested at the time, home to "thousands of wolves, bears, deer, foxes, wildcats, or lynx, raccoons, and other small animals too numerous to mention."

[17] An 1805 news report in York Gazette describes how a woman called Mrs. Munger shot dead a bear that attacked her neighbour.

[18] In 1820, Alexander Wood of Toronto build the Elmdale grist mill near the intersection of what is now Church Street and Highway 401; the site was later occupied a Latter-day Saint chapel.

Woodruff's sister Melinda married clock-maker Jordan Post, and their family acquired extensive lands in and around Toronto.

It served as a home for the family, and also operated as a stage station, providing service for stagecoach driver, passengers, and horses.

The store was very successful, and sold a variety of goods including groceries, clothing, footwear, glassware, light fixtures, hardware, and medicine.

The mill infrastructure was later expanded to included dams, a mile-long canal, a storehouse, and a Grand Trunk Railroad switch line.

The factory was not very profitable, and the stockholders criticized the board of directors for paying the dairy farmers over the market rate for milk.

William Peak (presumably a descendant of an earlier settler of same name) and others provided livery service, carrying mail and passengers between the two points.

Dr. Vernon-Cartwright was the first doctor to live in Pickering Village for a long time: he served there from 1917 to 1951, when he retired and moved to Burlington.

In 1965, the old newspaper press of The Pickering News was given to the Black Creek Pioneer Village in Toronto, where it showcased in the Dalziel Barn.

The earliest school buildings were single-room log houses, heated by a wood burning stove in the centre of the room.

[25] In 1867, Pickering's first brick school building was constructed at the southwest corner of Kingston Road and Church Street, in present-day Ajax.

[25] The building was abandoned in 1888, when a larger two-storey brick school was built on Church Street, north of Kingston Road.

[5] In early days, circuit ministers traveling on horses conduct serves at private homes, schools or public halls.

The Grand Trunk Railway supplied the bricks for the building, in exchange for a right-of-way across the south end of the Church property.

[33] In the early 1950s, the tower of the Pickering United Church was dismantled after being stuck by lightning, and was replaced with a metal cottage roof.

Rogers designated land for a large wooden meeting house and a cemetery on the east side of the Mill Street.

[34] The Hicksites later built their own Meeting Hall on the north side of Kingston Road, east of Harwood Avenue, opposite the Friends Cemetery.

[19] The Bible Christian movement met in a small brick church on the north-west corner of Kingston Road and George Jones Avenue.

It was called the "Pickering Post Office", and was located at various places near the intersection of Kingston Road and Church Street at different times.

[5] In 1942, the Pickering Village established its own civil defense unit, and 25 people signed up for a volunteer fire brigade.

[41] After a series of negotiations between the various municipalities and the provincial government, on 1 January 1974, Pickering Village merged with Ajax within the Durham Region.