The below article, a very lengthy article, is about as good as any in discussing the various methods we drill for oil, specifically for that oil in the Dakota's and Montana. Given the costs involved it'a amazing that anyone even does it! The actual good news is that, at today's crude oil prices, there is going to be a lot more drilling going on in those areas where drilling is allowed. As you'll see from the article it's not just a simple matter of punching a hole in the ground.
BTW, the genesis of the article was the belief by the author that the estimates by the USGS were too high for the Bakken field. But from the follow up comments it's seen that only technology will decide that matter.
FWIW, many of the same techniques are used in water well drilling in similar geological areas.
The Oil Drum | The Bakken Formation: How Much Will It Help?