"You can't get there from here." -- unknown roadside sage
Adventurers often do quite a bit of traveling, and roads make perfect locations for encounters, both mundane and unusual. The presence of a road indicates someone or something travels the route regularly, yet as a GM we often fail to consider exactly who these travelers are. A few minutes work can turn a boring, empty road into an interesting trip. Here are a few questions you can ask yourself to help bring your road to life:
Where does it go?
Roads connect things. Knowing what a road connects will greatly influence who or what uses it. It pays to consider not only local connections, but the bigger picture. To the locals a road might just be a way to get between two villages, but it could also be part of a byway that avoids an unfriendly tax collector or a shortcut that's only passable part of the year. Road connect not only destinations, but other roads. A villager might believe the road to the next village ends there, but a tinker or trader knows better.
The road's endpoints will help determine its course. Roads will tend to follow the easiest path between locations. Geography will play a great part in this, especially on major roads. Moving goods with draft animals or marching troops to their destination is easier on flat, open ground. Natural obstacles like rivers, ravines or mountains need to be crossed or avoided. Safety will play a role as well. A longer route through a well-patrolled area will be used more often than a shortcut through dangerous territory.
Who built it and how is it maintained?
In today's modern age, road construction is big business. In the typical fantasy campaign things may be less clear cut, but the origins of a road can add color to the scene. Was it a game trail that grew into a cart path? A significant trade route connecting cities? A road designed to move military forces along an unstable border? A bypass to avoid a hostile area? Once you know where it came from you can determine how it's maintained. Does a local government clear the verges? Is it overgrown and potentially blocked by fallen trees or rock? Is the route marked with blazes or mileposts? Are there bridges, tunnels or fords? Are they guarded? Are there tolls? Is the road patrolled?
Who uses it?
The meat of the matter, who travels this stretch of highway? The answers to the previous questions should provide some ready answers. A trade route will feature caravans, merchants and traders. A local cart path will have locals going to market, tinkers or farmers moving their harvest. A detour or bypass might have shady characters intent on avoiding authorities. Well patrolled and maintained roads will have a military presence and work crews in evidence.
Who supports the travelers?
Once you know who uses the road, you can figure out what services they might need and where they can be found. A trade route might be dotted with inns built to accommodate entire caravans. Free-wheeling mercenaries might frequent the area looking for work. On less traveled roads, accommodations might be less common, but a trading post, a farmer willing to rent a field for camping, or a traveling merchant might be more common. Busy routes will be more likely to have dedicated locals working to support the traffic, whereas on less frequented roads, travelers might be viewed with suspicion. There's also the matter of taxes, tariffs and tolls, all requiring some official presence along the route.
Who preys on the travelers?
Lastly, travelers will draw those looking for an easy mark. Highwaymen, corrupt officials, scamming innkeepers, card sharks and shady 'guides' will all appear if there is traffic to support their trade. Intelligent monsters might view the road as a good source of treasure and food. Not only will PCs traveling have to watch their backs, but they may garner suspicion from other travelers, who might view the typical adventuring party with some trepidation.
So there you have it, a few simple questions that should help develop the humble roadway into something a bit more interesting. Using these simple questions as a guide coming up with a few encounters for any roadway should be pretty easy.