Traveling often doesn’t need to be part of the story. This has been talked about by people who have thought about it more than me, and the advice typically is: don’t bog the game down with traveling. There’s no need for combat to show off how dangerous the world is. There’s no need to take a whole session of play getting from A to B when you’re trying to show off how far away two points are.
Just use your words.
However, on special occaisions you might want something fun to happen during travel. Here’s a d12 list of ideas for you to use on those occaisions.
I tried to do a d20 list, but it’s actually tricky to add interesting events without distracting from the story you’re trying to tell, which presumably the players want to get on with. (With the exception of number 10, which was just fun.)
1. Rain has been ceaseless. Travel difficult and slow. Make a Con save. The DC is 15 if you’re travelling without tents, with a tent the DC is 10. A failure means you’ve become ill – a mundane cold or slight fluu, but none the less it sucks. You are as if Poisoned until you find medicine or 1d4 days of comfortable rest has been acheived.
2. 1d4 crows – huge ones! – appear and fly nearby for a while. They harmless follow you, curiously. If you choose to befriend the birds, make an Animal Handling check (DC 10). On a success, the crows enjoy your company and are wiling to keep an eye out for you, even joining in battle when outside.
3. You were attacked by 1d4 salamanders. You dispatch them easily. Roll a Survival check (DC 10). On a success, you’re able to disect the animals and extract their poison glands, which are quite valuable. In the right hands, they’re also a good coating for your blades.
4. Make a Perception check (DC 10). On a success you come across a recently buried cache in the ground; it contains 1d4 simple weapons (one is silvered), some bread, water, and some cheeses. There’s also a love letter/death threat/written oath in the box.
5. Make Dexterity saving throws (DC 10). Your camp fire erupts for some reason, scattering burning ashes. On a failure, the embers catch your clothes. They’re damaged now, requiring light mending.
6. Whilst foraging or looking for water, you come across a natural beehive, filled with 1d4 litres of honey. It’s delicious (and valuable), so long as you have a way of carrying it.
7. Throughout your entire journey, at night, the voice of a weeping person could be heard. They sometimes yell a name into the night, but you’re unable to tell which direction it’s coming from. This happens every night. Make a Consitution saving throw (DC 10), or you arrive at your destination with one level of exhaustion.
8. Sometime into your journey you meeting another traveller who is just leaving the general direction of your destination. They stay just long enough to answer two questions; one will be a truth and one will be a plausible lie that the players should corroberate before acting on.
9. Your horse has taken an injury – painfully broken ankle or stone in its shoe – and is unable to carry the burden of your baggage. You’re slowed and need to carry your own cargo. This may mean that you need to leave something behind if you can no longer carry it. Maybe it’ll still be there next time you come by this way…
10. A man lies dead on the floor and a shimmer of a portal – barely visible – still lingers behind him. It is stable and leads to his home which for some reason he was escaping from. Side dungeon!
11. Your journey coincides with the travelling of a circus/bardic band/priest. Along the way you helped them by sharing rations or forraging extra food for them as they were running low. They owe you a favour, which they’re happy to pay at a later date. (The currently have no money.)
12. You find a spellbook/holy book/Tome of Honourable Deeds/natural observation log. It lists a spell, ritual, or enchantment you’ve never heard of before. In fact, no one has. No one is able to deceipher it. It grows warm when it is most needed.
