How old are the settlements? They'll spring up near the interface between plains and forests for the farmland on the one hand and the building materials on the other. As a settlement ages, more and more of the woods will be consumed. Depending on the government, some of the woodland may be protected from cutting as crown forest or nature preserves, or whatever. In short, the older the settlement, the further it is likely to be from the edge of the forest.
Settlements will likely appear about half a day's travel from one another if terrain permits—far enough to go to the next town over, do a bit of business, then get back home. How far that is depends on the available common transportation.
Rivers make travel easier and faster, so a civilization will spread out more quickly along waterways, but it will also meet competition sooner, so the oldest towns will probably be on the rivers. And in spite of water travel being easy, there will probably be roads parallel to the rivers for shorter jaunts that don't justify a boat. Towns will also exist near easy fords and/or bridges, and they're quite likely to pop up at a confluence of two rivers.
Remember that rivers in lowlands are prone to changing their course. Sometimes humans prevent that with artificial watercourses, sometimes the towns follow the water, and sometimes the people are just stubborn enough to stay put.
The style of agriculture will shape where the farms go, and the land and climate will determine the style of agriculture. Usually. So in order to determine where the farms are, we'll need to know a bit about the land—are we talking Mediterranean, northern Europe, Great Plains? I'm guessing a somewhat northerly climate because of the pine forest, but cedars grow in the Mediterranean, so that's not a gimme.
If the government isn't deciding where they should go, roads will connect settlements by the most direct route that is practical. "Roads are made by the walking," after all, and people don't like to walk farther than they have to. Roads that appear in this manner are unlikely to be paved or otherwise maintained. And they may not be adequately mapped because they're most often used by locals.
Okay, I should be doing work right now instead of writing worldbuilding essays.