Stonetop is a Dungeon World adaptation, where the PCs are all the heroes of an isolated iron age village. So when they go on an expedition, it’s almost always to either deal with some sort of threat to the village, and/or to seize/explore some sort of opportunity for the town (or sometimes the specific PCs).
So the core assumptions are the the PCs are going on a journey with a specific purpose in mind (not just exploration for the sake of exploration), and that they’ll usually return home. The scale is relatively small, too (the longest journeys you’re likely to take in the game are maybe like two weeks each way), and there’s a starting map of the region with a number of points of interest. Plenty of blanks, and lots of player-created and procedurally-generated content.
When the PCs want/need to mount an expedition, they Chart a Course, which is basically a Savvyhead Workshop style move where the GM lays out the likely courses, how long they’ll probably take, the requirements (“you’ll need warm clothes and snowshoes” or “you’ll need a guide”) and the challenges they can expect to face (“you’ll need to watch out for hunting drakes on the Flats” or “the way will be grueling”).
When the PCs actually head out, you do point-crawl style travel, dividing the trip up into legs of travel and points of interest.
On each leg, if it’s unfamiliar-to-the-players terrain, you describe (or get the players to help describe) the environment, ask questions to each about how they’re experiencing the trip, what they’re talking/thinking about, etc. If this leg would involve one of the challenges established when they Charted a Course, the GM drops it on them. Otherwise, maybe we do some role-playing, maybe the GM throws in some unexpected encounter, but more likely they get to the next point of interest.
At each point of interest you zoom in and have a scene. These can be landmarks that haven’t been seen in play before (in which, you describe them, ask questions, maybe do a little roleplaying, and then likely move on). And/or they can be places where you know something interesting will happen: an ambush site, a mystery to explore, a crucial decision to make, an obstacle to surmount.
Basically, you’re playing out the legs and points in much the same way that you’d handled a dungeon-crawl, just a bit more zoomed out and with a lot more time spent on reflection and Q&A. I find that asking each character questions about their experience of travel creates a sense of time and distance passing, in a way that you don’t get when you just say “okay, the next few hours are uneventful.”
But also, one of the principles of Stonetop is portray a rich and mysterious world, and spending time fleshing out new-to-the-players parts of the world is a big part of that.