In the 1700s, farmers migrated to the Overberg region in search of good farming lands. Many settled around the area now known as McGregor, due to its fertile soil. As the settlers in the area were extremely religious, a church was first built, and the town grew around it.
The town of McGregor was founded in 1861, originally named Lady Grey. It was renamed in 1905 to honour Rev Andrew McGregor, who had been the Dutch Reformed Church minister in the Robertson area for around 40 years, and played a vital role in the development of the region. When plots in town were being auctioned off, it was said that a main road to Cape Town would be built right beside the town. The road was never built, and McGregor remained on the outskirts of the region (as it still does today).
McGregor’s irrigation system dates back to the 1800s. A water channel was built at the edge of each street that feeds water from the town to the nearby dam. Each landowner now has a slot allocated during the week where they get a few minutes to an hour for the channel to flow into their property to water their gardens.