This is done by rolling a d8, d6 and d4 at once and consulting a chart. One die for terrain, one for people or thing encountered and one for "the twist".
An example might be as follows:
The Main Highway: 5 points
Terrain:
1: Flat open plains for miles
2: The road crosses a small river at a bridge
3: The road moves through a light woods
4: Flat farmland, in the distance a barn.
5: A small hamlet
6: Light hills
7: An Inn
8: Gently rolling hills, some shrubs
People and things:
1: Nothing
2: More Nothing
3: Passing travellers (2d6) with a wagon (if 5+ travellers). Police/Military if total dice 13+
4: Danger! (Bandits if dice total 13-15, Wild Animals if 6-12, Large Monster on 16)
5: Caravan (Gypsies if Total dice is odd, Merchants if even)
6: Roll Twice more...
The twist:
1: Nothing
2: Shortcut (+1d4 travel)
3. Detour (-1d4 travel)
4. its Raining
This works best with other travelling options. So maybe rather than taking the main highway the heros want to take "Hellscape Pass"
Hellscape Pass: 25 points
Terrain:
1: A narrow winding path along a sheer cliff
2: A deep valley
3: A dillapidated rope bridge over a chasm some 300 feet down.
4: A rocky slope, tiring but able to be walked
5: Dense Pine Foothills
6: A glacier
7: Shattered ruins of a dwarven fort
8: Rapids leading to a massive waterfall
People and things:
1: Nothing
2: The Great Dragon Oerliken, with his 20mm dragon breath (unless already killed).
3: A cave entrance (Treasure if total die is 8 or less, roll once for inhabitant).
4: Orc Warriors (equal to twice total)
5: Eerie quiet(avalanche if loud noises)
6: Nothing if total is 13 or less, otherwise 3d6 Yeti.
The twist:
1: Nothing
2: Roll Twice
3. Haunted (ghosts come out at night, but avoid fire)
4. its a blizzard
Thus a party might be told, "City B is 30
