Now that I wrapped up my long winded commentary on Dungeon World, something positive did come from my abbreviated read through of the book. I really liked the way the book handled traveling and random encounters and such.
For those that haven't played the game, in Dungeon World, when the PCs travel, one PC is the quartermaster, one PC is the scout, and one PC is the navigator, or words to that effect. Each one makes a check to see if you use more provisions than you expected, if you run into monsters, and if you get lost.
I like this idea. While the wilderness has, from olden days in D&D, had it's own kind of rules compared to the dungeon, there is kind of a binary issue with overland travel. Check for everything every day, and things drag to a mechanical halt. Not only that, random encounters multiple times per day due to bad die rolling seems silly, but changing those encounters because they seem silly makes even making the check seem pointless. On the other hand, just saying "you traveled for a month" seems pretty anti-climatic.
Now, the reasons for a quartermaster in Dungeon World have to do with provisions have their own special mechanic that ties into resting and the like, so it's not as important for this discussion. However, navigation and scouting do make some sense to export. So I tried this for my Dungeon Crawl Classics game.
For every week, the PCs make a navigation check and a scouting check. If the trip is less than a week, you make one check each, minimum. If you fail a navigation check, you add a week to your trip (or a day, if it was shorter than a week). For each week, you make a scouting check to see if you run into a random encounter. PCs that don't want to scout get an encounter, and you shouldn't feel guilty about slamming them with 1d4-1 wandering clones of Orcus. Or something like that.
I liked it, and it didn't handwave the travel time, it just gave the PCs something they could do to mark the passage of time that was relevant to one of their backgrounds (or not, since it's DCC and not everyone is going to be good at navigation and scouting). If you want the area to be more likely to have wandering monsters, or be overgrown and hard to navigate, you just up the DC. In a well patrolled area with tons of formally paved roads, you bump the DCs way down.
Now if I could just come up with a good way to incidentally include weather in a fun, encounter based manner that didn't bog things down as well, I'd be thrilled.