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Message: <blockquote data-quote="gizmo33" data-source="post: 2872128" data-attributes="member: 30001">This is a really interesting question that greatly impacts the way that DnD is played and yet IMO there's never really been a lot of guidance on this issue.I agree that boring encounters during overland trips are not worth it.  I try to flow-chart the long-trips in my campaign, but that only works when I have some advanced notice that the PCs are going to take the trip.  Otherwise, I tend to fast-forward.DnD works well in dungeon settings because the PCs know what they're supposed to do and the DM only has to be prepared for relatively few contingencies.  Plus interesting encounters are grouped close to each other, and there's plenty to do for all the characters.  I would think that interesting travel or down-time scenarios would have these same characteristics.  This is the basic position of the Heroes of Battle book, which tries to make mass combat interesting in this same way.The Pendragon game system has rules for down-time.  The framework is that you adventure once a season, and then roll on a chart to determine what you character does for the rest of the year.  The system seems designed for players to develop families of knights and play over several generations.  Did anyone have any experience with this game and are there elements that could be used by DnD to address the second part of the OP?  (Of course I can imagine some players saying "but my warforged ninja doesn't want a family!" so YMMV)</blockquote>

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