Down there in the lower right corner is the "scale" - it shows the distance of 2, 4, and 6 miles.
Look at this link to see how fast people move. If the slowest person in the party is movement rate 30, they can travel 24 miles in a day. If the slowest person is movement rate 20, they can travel only 16 miles in the day. Cut this in half if the terrain is difficult - all these rules are on that page I linked.
Now measure that "scale" with a ruler to see how long it is, then lay that ruler down between where they start and where they're going to see how far it really is.
For example, it looks like from Falcon's Hollow to the western lumber camp is pretty close to 18 miles of decent terrain, so a party of humans (traveling 24 miles in a single day) can make that trip in less than a day (about 6 hours of walking).
Another example, from Falcon's Hollow to the Dwarven Monestary is about 24 miles and most of it is through the forest with no roads. If they're all humans or other 30' movers and they go in a straight line, it's about 6 miles (2 hours) to edge of the forest (about at the middle of the "H" in "Halfway"). Then it's about 8 more miles to the river, through forest (rough terrain, half speed) - that would take a little over 5 hours (1.5 miles per hour) so they reach the river at the end of the first day of travel. They have enough time left to cross the river today so let's assume they do (and have no troubles with it). They camp on the far riverbank (that river looks like it's at least a mile wide so I'm assuming it's not really to scale). Then it's about 9 miles to the monastery, at a 1.5 miles per hour, so 6 more hours to get there (before the end of the second day).
See? It's simple.
(It actually is, it just seems tricky when you're trying to figure it out for the first time).
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I am currently running HLH...
According to Page 5 in the module...
The entire journey, from Falcon’s Hollow to the lumber camp, to various forest locations and on to the old dwarven ruins, is just over 37 miles in length. Assuming the group moves at a speed of 30, the entire
journey takes a little more than three days, plus any time spent exploring or days spent resting. This time increases to five days if the group’s speed is 20. Crossing the water on the return trip cuts it down to only 22 miles but requires a treacherous swim or the construction of a crude raft.
It's 11 miles from Falcon's Hollow to the Lumber Camp, 5 miles north to the lake, 9 miles to the Elder Darkwood Tree, 6 miles to Ulizmila's Hut and another 6 miles to the Ruined Monastery.
If your party is moving at 30 speed, they will need to rest when they reach the lake. (More than likely after the Grunge Knifetongue encounter.) You will want to roll their first random encounter after they leave the Lumber Camp and enter Darkmoon Vale.
Next, they will head north to the Elder Darkwood Tree.
The party should rest before heading to Ulizmila's Hut, they can rest either before or after the second random encounter between the two locations.
The party can continue on to the Ruined Monastery, but they will roll a third random encounter and it will be dusk or dark by the time they reach it and might trigger the wolf encounter on Page 9.
The party can enter the Ruined Monastery that night or choose to wait until morning.
So it goes like this:
Day 1: Falcon's Hollow --> Lumber Camp --> Random Encounter --> Lake *rest*
Day 2: Lake --> Random Encounter --> Elder Darkwood Tree *rest*
Day 3: Elder Darkwood Tree --> Random Encounter --> Ulizmila's Hut --> Ruined Monastery *rest*
Day 4: Enter Monastery
If your group is slower, then it works out like this:
Day 1: Falcon's Hollow --> Lumber Camp *rest*
Day 2: Lumber Camp --> Random Encounter --> Lake *rest*
Day 3: Lake --> Random Encounter --> Elder Darkwood Tree *rest*
Day 4: Elder Darkwood Tree --> Random Encounter --> Ulizmila's Hut *rest*
Day 5: Ulizmila's Hut --> Random Encounter --> Ruined Monastery *rest*
Day 6: Enter Monastery
Hope this helps! My group has had two sessions and hasn't even made it out of town yet. Shoot me a message if you have any more questions.
Oh and I created a side quest if you'd like to use it. If your party stops at the Sitting Duck and speaks with owner Elgin Tock, he offers to pay them to gather ten Appleleaf plants so he can brew a keg of Appleleaf Ale. Laurel has three of them hanging in her shop and the other seven plants can be gathered on their travels through the Vale. Use a Nature Knowledge or straight Perception to find the plants. Just more fun stuff!
Good luck!
~ Jason
Wooooow dude, thank you so much! All of you! And also thank you for sidequest! But, how do you know a name for the owner? You made it up? Or is it from another adveture? Last question, about swim check. Is it just one DC 15 check, because of rough water? Or it's more complicated? And what DC is for making a raft? Is it high-quality item or typical item?
There are three resources for Falcon's Hollow information: The modules, (Hollow's Last Hope, Return of the Kobold King) Towns of the Inner Sea and the Guide to Darkmoon Vale.
If you don't want to buy the books, the Pathfinder Wiki will provide you with most of the info.
http://pathfinderwiki.com/wiki/Sitting_Duck
Good luck!
In my opinion, the random encounters are meant to show the passage of time. These are long distances to travel through heavy forest and you want to show that time is passing. Also, most of the random encounters do not involve combat.