If you regularly drive to the same places, then it is probable that you usually take the same routes each time to get to them. That could be problematic.
Familiarity can breed complacency. While that is true in many areas of life, it can be of particular danger when driving. As a driver, you need to be alert to what is happening around you. If you are on autopilot, then you are not.
Autopilot may not account for changes
If you remove all other vehicles and pedestrians and drive the same route repeatedly, you will likely get home safely each time. The more you drive the route, the less mental attention you need to give it.
The problem is that real-life roads are not like that. They are slightly different each time you drive them. While the road surface may be the same, except when weather conditions change, other vehicles and pedestrians add a constantly changing set of variables.
A pedestrian may never have crossed a particular junction the previous 55 times you have driven a particular route, but that does not mean they won’t at some point. If you are on autopilot the first time they step out into the road, it may be the last time they ever can step out into a road.
While following the same route does have its advantages, if you find yourself becoming too familiar with a route and realize you are missing things, it may be time to change it up. Not only does it reduce the chance you will cause a crash, but it reduces the chance you are caught out and injured by another driver who is drifting along oblivious to you.