I would like to build on some of the earlier posts which suggested the natural growth of a trail system between settlements. My suggestions are based on my observations from an earlier period of life when I spent a great deal of time living in wilderness areas in North and South America.
Encampments would spring up naturally around resources (like our cities will). The better the resources the faster the growth of the encampent (again like our cities). Given a minimal size of nearby encampments, people start to go back and forth to visit, find romance, tell stories, and trade items they can easily carry. Therefore the early trail springs up automatically, no investment needed, on a pretty direct route.
If the encampments grow sufficiently eventually traffic will increase to where there are not just people walking but now they want to use a mule to haul grain or ride a horse back and forth. Perhaps the trail will move slightly to avoid the branches and narrow spots or perhaps the people will cut down some trees to make the trail wider and drop a tree across the creek to make an inprovised bridge. The trail is now better and faster, minimal work has been put into it, but some work has. However, it is still a trail, not a road and no investment is needed, it naturally grows when population does.
If the settlement grows to where it is a real town there may arise a need to start pulling carts of food or wagons of trade goods back and forth. Now we need a wide trail without steep grades and with either fords across the streams or basic but solid bridges. We can no longer take the direct route across the ridge and wade the creek, we need the longer route over the pass and to the ford. Rocks need to be moved, potholes filled in, solid bridges built. Now we can move real quantities of grain, ore, manufactured goods and the gentry in their carraiges. At this point government usually spreads to the outlying encampments since tax collectors follow the goods. This level of road requires some investment but not a professional building crew. Town growth would be slowed if the investment is not made.
The next level is what we would call a road. The route is laid out by engineers, we lay stones, we spend a great deal of time and money building a real bridge. This road is much quicker to travel and can accomodate heavy loads (such as siege equipment) and fast travel, such as cavelry. This kind of road needs to be built by a professional. It is a significant boost to the economy and connects major cities.
In Summary:
- level 1 trail, automatic, slightly faster than cross country, no upkeep
- level 2 trail, automatic upgrade on time and population, faster travel, no upkeep
level 1 road, minimal cost, no specialized unit needed to build, faster travel, improved commerce, probably no upkeep, tax bonus
level 2 road, specialized unit needed to build, significant cost, very fast travel, very solid bonus to economy, probably rare to see these except between very large valuable cities after the passage of significant time.