Overland travel is generally not too complicated, but if you don’t do it often or haven’t handled it before it can be a bit intimidating.
Get your players to establish a routine at the beginning of an extended trip of how they will handle things like setting up camp, setting watch, and marching order. This will make it easier to determine what who is where when stuff happens.
If the party is on the way to the dungeon, next city, etc. then any encounters should motivate them to reach their destination. Older modules are full of charts for random encounters that happen during overland travel. I try to steer away from random encounters as much as possible. If you have encounters prepared (and you should) then insert them into the travel when they will have the biggest impact on the players.
Unlike a dungeon, overland travel encounters are generally a matter of time rather than of place. If the journey from village A to city B takes 2 days, then you need to decide when during that trek the encounter will happen.
If the encounter is a group of thieves waiting in ambush, then it should happen while the party is travelling, not camping. If they are hired assassins, then they will strike when the party is most vulnerable, usually during a rest period. You can have a lot of fun creating the timing of the encounter. Striking just as the sun begins to dip when shadows are at their longest in a murky forest, or rising up from the grass on the windswept plains can offer some interesting surprises.
If the party is on an extended trip and will face several encounters, then you have a great opportunity to really play with the timing. Do the Night’s Assassins always strike at night? The party will catch on quickly to timing like this, even going so far as to reverse their schedule, trying to rest during the day and travel at night to throw off the attackers. Or do the ambushes happen irregularly or appear to be random? Think through what personality traits drive your NPC’s and the players will enjoy it more.
Remember to include all your overland encounters in your overarching XP and treasure levels. All too often the random wandering monster doesn’t have any treasure. After a few of these types of encounters the party’s resources can be drained or their XP level will outweigh their treasure.
As always, have a fun game!
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