2020: My Country

To build a road, you need to click on the yellow hard hat button, then on the road symbol. You can build roads at any time, and each grid square with a piece of road on it counts as a roadway. To build 1000 roadways, at $400 a pop, you will need a total of $400,000 in total for this, so it is probably best to wait until later on in the game when you have a decent amount of cash in hand. When you have just purchased a new territory, fill it with roads and then use the bulldozer to demolish them. Rinse and repeat until you have 1000.