As mentioned in chat with Emirikol in another thread, games like One Ring and Mouseguard have ideas to steal from.
I used One Ring's "roles in travel" to come up the following approach to travel in my latest homebrew adventure that involved following a beastman band with captives from a raid on Frederheim to ther lair.
A design note: this was all considered 1 Act (there had been one "all make a Fear check" before the travel part so this means there are 4 mandatory checks in the Act for each character plus possibility of others - I figure that's a respectable number for an Act and then Rally step).
On all these checks an urban character suffers a misfortune die; a rural character gains a fortune die.
Roles of Tracker, Scout, Morale Booster [Leader] and Provider are taken by characters (I did a summary sheet of these in 4 large boxes to put stand ups on to show who was which.
Tracker : Average (2D) Observation (Int) (tracking), failing adds a Challenge Die to the Resilience checks of all characters as lost time must be made up. Triple Success reveals there are 14 or 15 beastmen in the group. On a success, each two boons on the check adds a fortune die to all individual Resilience checks.
Scout: Average (2D) Stealth (Ag) (silent movement - rural), failure means a Bear Encounter takes place, success avoids the Bear. Chaos Star on failure means the check in encounter has 2 misfortune dice.
The Bear - as you cross a clearing you see a black bear with several young in the trees on other side. The bear notices you, it growls menacingly.
Animal Handling 3D check to avoid a confrontation with the bear in which each PC rolls 2 misfortune dice and takes 1 wound for each failure and 1 Fatigue for each bane
Morale (what a leader would do: (this is relevant upon upon encountering the dead captives): Average (2D) Leadership (Fel) (military), failure means that the sight is troubling and all must make a Fear (2D) check, success means that the scene can fuel righteous anger and allow recovery of any combination of 2 in Fatigue and Stress. Characters in a combat or military career do not have to make the check as they are innured to such sights.
Dead Captives – you come across the remains of a man and woman in the shifts worn by inmates in Frederheim. They have been lashed to two trees and mutilated, it appears large chunks of their flesh ripped out.
Provider: Nature Lore (Int) (2D) (narrate which) to avoid natural hazards and benefit from possible sources of aid. Success means that as many doses as margin of success of a useful herb such as Valerian are found (note still requires preparation to use). Failure means that heroes are exposed to brambles, unpleasant conditions etc., adding two misfortune dice to the Resilience check.
Event
- the path leads to a river. The river is wide, with a steady current but not a particularly treacherous one. A good swimmer could cross it safely but failing in the attempt could be dangerous. It can be swum across with an Average (2D) Athletics (swimming) check – failure means suffer 2 Fatigue and try again, repeat etc. (passing out means drowning unless rescued). Encumbrance truly hinders swimming, having Enc > Str is one misfortune die, > Str x2 is 2 misfortune dice, etc.
- Using floatsam or logs to help cross can add a fortune dice to roll – this is an Easy 1D use of Nature Lore an adds as many fortune dice as successes rolled.
The Final Resilience Check
- ALL
All heroes then must make an Average (2D) Resilience check to see how well they have held up by the time they reach the next Act. Failure means 2 Fatigue. A Chaos Star and failure means a negative condition suffered (Under the Weather or Demoralized - random).
If everyone succeeds, the group travels faster and arrives sooner. If anyone fails, the group travels slower (arriving sooner makes a difference in the adventure).