Yes Mandala is the town just right of Richmond Castle.
You are free to bypass it, but that would require going off road. I figure it would just be faster and easier to go through...
Woodstock is where the road ends in Hood. The reason it is shown as huts is that it is a temporary settlement.
The Red huts icon is the Goblin settlement. (the exact location is unknown as they are nomadic.)
The red icon at the top is an old ruin predating the current age. (but the characters don't know about it)
The small tan huts are logging camps feeding into Woodstock. They don't have names, and they move every few months.
For this leg of the journey you have complete freedom to role play interactions with the farmers, merchants, etc. (so long as you keep it reasonable

)
And when you reach the border it is going on evening, and time to make camp.... There is a well used cam site at the border.