'So Maltag, which way to Zartin the Elder's hidden tower?' Sverna said. 'Well I do believe its that way, as the mole burrows.' the dwarf pointed down to the valley below. 'I wonder what trouble awaits us there.' Sverna pondered. 'Don't be worrying about that we have company, Werebadgers!' Maltag spat. Snaring ill tempered werebagers charged out from behind the rocks.
Wilderness travel can be both perilous and wondrous. What is just over the hill could be either or even both. Exploration of the wilderness is an arduous take both for the player and the game master. There is less control for the game master being outside the dungeon. The players may wonder anywhere, even off the map.
The most basic tool is a map. Before the adventure have a map of the region and a variety of terrain features. Start the adventures near the center of the map or near an area they have been too before. Have two copies. One for the game master and on for the player. The player map has the areas they have traveled through to get where they are now and the game master has one with all the detail. Up date the players map as they go along. Either by telling them what type terrain or just drawing on the players map.
Wither it is grid, hex, or plain free form map it is up to you. A good rule of thumb is to have at least three different terrain types on the map.
Then add some sub-terrain types as well to give the map some depth.
Create at least three encounters for each terrain type. One major, one intermediary, and one minor. Don't assign them to the map but when the players are in the terrain type either roll randomly for an encounter or decide when it is the right time. Remember not all encounters are hostile.
Also have some pre-made 'wilderness window dressing'. These are objects, sites, and oddities that the players encounter.
Wilderness Window Dressing
A large stone covered in carved spirals.
A pool which reflects the players trues selves.
A large burnt oak with a twisted face.
A glyph of a dragon carved into a hill.
A set of bone wind chimes hanging from a tree.
A abandoned gypsy wagon covered in moss.
Also a traditional random encounter table based on the region may be helpful as well to flesh out the area. So when traveling trough the Fang Hills there may be a lot of werebadgers.
'Sverna are you wounded?' Maltag questioned eyeing her weary. 'Nope not a one got with claw raking distance.' Sverna said relieved. 'Lets put as much distance from the werebadgers and us as possible. By the Forger's Braded Beard! That hill in the distant it has a outline of a dragon and its glowing!' Maltag exclaimed. 'I'm still sharp if you are greybeard' Sverna smiled. The two trudged out of the Fang Hills. In the distance the moonlight illuminated the outlining of a dragon and dancers upon the hill.
Toes - I haven't been using my running sandals for a few months, now.