Maybe off-topic with the current topic, yet surely on topic with the game. Anyway... my ideas(?).Offtopic, but I wonder if one day we will go on the island, probably we will start from that harbor.
That fortress could either be an outpost of Parakis or a ruin, those big yellow things inside look like tents?
The more I look this map, the more I notice new details, like the Stonehenge near the inn, a cemetery and... is that a pagoda? Or a structure from the east near Parakis?
Maybe Anya knows something
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Dwarven Fortress Ruins - The ruins in the upper part of Darkwood are probably of Dwarven orgins, being a fortified gatehouse of thier moutainside stronghold. Because who would, in the right mind, build a fortress in the moutain side overlooking thick woods of darkwood? From the strategic point of view it just doesn't make sense to build such a great structure so far from the routes and settlements.
Some weird rocks - Stonehenge. A teleport to our world!
Dontcare island - A island of rather strategic importance to both sides of war if you ask me. Having the island means controling the waters between frontline and Vale of Karantis and being great base of operations for a naval assault. Lord Shortquaad (or was it Farquaad?) could just keep some of his forces at Spitroast bridge to keep the other lord from advancing, and just send a naval assault on the harbour to cut off the supplies, attack enemy rear or do both, or swim further up the waters, land near abandoned monastery, turn it into a war camp and launch a assault on Kirlic or even Parakis.
Tight Moutain Pass Castle - A castle of rather strategic importance. It's overlooking and protecting the one of two main, and only two, routes to Darkwood valley. Controling it, means controling anything from Parakis and Kirlic to frontlines or from frontline and Arenfield to the other side.
Red Cross - A great location to build a second castle, because of great location. Just as Tight Moutain Pass Castle, just from the othe side. Having both in MC's grasp means controling the Darkwood and forcing Lord Farquaad to take alternative (blue lines) route to the frontline.