At the end of my last gaming session, Ivy Blacksword found herself in possession of a new warband and vowed to conquer Eveningstar. I took a long break from the game to stat up Eveningstar’s defenders (Lady Winter, her knights, and the local monks), and to think of what to do next.
All told the warband consists of 27 HD worth of creatures. At present, only the four party members have any equipment. The former prisoners are serving under duress, dressed in rags, and have low morale. They have no food or drink, although the bugbear cave is well-supplied with both. There are also bugbear-sized maces, shields, and blankets available. Against this force are Eveningstar’s 169 HD of defenders (not counting any adventuring parties who may fight in the town’s defense). Lady Winter and her knights all have warhorses, while Ivy’s warband are on foot. Her troops are untested and liable to desert or fight amongst themselves at the first setback. Harg the bugbear is loyal, fortunately, and for the moment at least Heinryk the Hero appears to be. The elves, dwarf, and two other humans can be counted on to obey orders, but not necessarily to fight. For the orcs and goblins, the reverse is true: they’ll happily burn farms and loot the town if they can, but won’t do labor if they can help it.
Ivy may have plans of conquering the town, but I begin to see why none of the monster bands in the caves have managed it so far. With Blackstar in her hand she’s an even match for any one of Lady Winter’s knights in single combat, but her odds in a military campaign seem insurmountable. Still, she has at least three advantages that she knows of, and one that she doesn’t:
Eveningstar doesn’t know that she plans to attack.
It’s almost harvest season. The militia will take longer to gather, and the thanes will be slower to respond and eager to get their followers back to their fields to bring the harvest in.
The Caves are difficult for either horses or the militia to assault.
A more immediate problem are the other inhabitants of the Caves of Chaos. There are:
2 bugbears (HD 3, returning from a hunting trip tomorrow)
14 male gnolls (HD 2)
20 female gnolls (HD 1)
1 gnoll chief (HD 3)
1 minotaur (HD 6)
1 owlbear (HD 5)
3 slimes, 2d6 giant rats, 13 stirges, and 5 fire beetles
Counting just the active monsters, that’s 61 HD. The gnolls alone outnumber her little band, and are already unhappy with Ivy for sending back one gnoll prisoner carrying another’s severed head. Reactions for the bugbears and minotaur have yet to be rolled (owlbears, naturally, are hostile to everyone). Depending on how things at the Caves shake out the town may never know it was threatened at all.
Her first moves will need to be to secure her position here in the Caves. I don’t think she can make her recently-freed prisoners move quickly without food and rest, so the gnolls will have plenty of time to respond while she loots the cave, arms and feeds her followers, and so on. After that (and barring an assault by angry gnolls) her plan is to head for the goblin and hobgoblin caves. The bugbear lair only has one exit that she knows about, making it easy to lay siege to. Furthermore, the cleared goblin lairs contain an armory and a cave full of supplies. If she secures those she can arm her followers and feed them for a considerable period. She’ll need to cross the gorge and ford the Starwater in order to reach it, however. The gnolls will likely see them coming, and her followers will be particularly vulnerable during the crossing.
Assuming all goes well, she may be able to make contact with the bandits in the Briarwood through Robart and Delgert. If she can forge an alliance, she’ll add 13 HD of disciplined, well-equipped troops to her cause. She may be able to bargain with the minotaur as well, although "Keep on the Borderlands" informs me that he is “fiendishly clever” and is accustomed to taking payment in live humans, which he eats. The owlbear may have to be killed if she remains camped in the gorge for a long time, although she has the advice of the cave-dwellers to help her avoid it. Rivior’s ghost knows a great deal about the Haunted Halls (having constructed them in life), but they’re even less secure than the Caves. The mad king is surely paranoid about being trapped and starved in there a second time. Still, it’s just possible that she could rally the immortal/undead curst to her banner, and Room 17 holds Rivior’s consort, trapped in a temporal stasis…
All told, Ivy’s options in case of a defeat are pretty bad. Eveningstar blocks the way south, so she would likely need to retreat north into the Stonelands, where supplies would become an immediate problem for her ragtag army. It is perhaps just possible that Ivy and Tessaril could work out a peace agreement, with Eveningstar ceding the Starwater Gorge to Ivy and in exchange for outsourcing defense against attacks from the Stonelands. Ivy would want to levy a toll on all wealth looted from the Haunted Halls, however, while Lady Winter would want an oath of fealty that the ghost of King Rivior would not let Ivy swear, so it seems unlikely. Maybe some enterprising young adventurer who is popular with the townsfolk and has a history of improving his land will some day earn the right to settle Starwater Gorge…

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