This is a map I made but did not use. Let me discard it here.
It starts at the northeast corner. The adventurers want a better life in a warmer clime. They themselves don't have a map, but they have an itinerary: walk east, hit the sea follow the coast south until reaching the right place.
The road traces its line just south of the three oaks mound. Climbing an oak gives a good view on the region, one sees the smoke of the fires of Northport, but not its houses. The mountains in the south are just hills then mountains, with lots of fir trees.
A bit before Northport, the coast forces the road to go southeast and at some point, there is a fork that descends to the town. Grass seems to win on the south road, while the fork to Northport is well defined.
Northport is a sleepy fisherfolk town. Travel by sea to Southport is possible but requires paying some kind of fee. People there declare the mountain road to be closed because of some not well remembered evil.
Travelling by fishing boat on the sea road should be straightforward. Where the mountains dive in the sea, there are many places where to hide and take a break.
Right before the first hill, the mountain road divides east and south. The east branch seems easy and avoids the sudden climb that marks the beginning of the south branch.
There is a charcoal kiln at the end of the east branch. There are lots of pine stumps around the kiln but no adult pines. the place is rather desolate and the kiln was almost drowned in an mudslide a few season ago it seems.
The south branch climbs and then plateaus and reveals a decrepit toll outpost at the pass. It chokes the point where the road goes through the rocky spine and the descent begins.
The southern slope welcomes the character with clouds seemingly blocked against the mountain, sometimes rain, sometimes fog. When the hills are over, the decidous forest continues and it gets somehow warmer.
The road traces across the meadow and reaches a fork with two elms at left hand. There is a town by the sea and the road, to the right, leads further south.
Southport is a trade town with double the population of Northport. Lots of opportunities and new chapters there.