Dar's expression remains studiously neutral when the group starts talking about the Iron Circle. "Well, you're a brave bunch! I'm sure you'll be able to do whatever you put your mind to! Afraid I'm not much for politics myself, since everyone needs stables. Now, are you fine people needing a mount?" Pointing at a grey riding horse, he says "Sylvia over there is a strong beast, I could lend her to you for today, for just five gold."

"Is she brave, too? We might need some mounts that don't flee of a battle, if we want to free the baron" Quyst says firmly, trying to make Dar realize that they are allies.

"The five of you all alone in a battle against the Circle? Well, that will certainly be a fight to watch! I'm sure Sylvia would serve you, although I wouldn't want her to get hurt!" While he pats the horse's neck, Dar's face doesn't betray any change, besides a slight mocking smile at the thought of five adventurers riding alone into war against a trained army.

Ursula introduces herself to Dar Gremath as well and then hands him the letter from Branna of Tor's Hold. Lord Gremath, respect t'you an' all, but it ain't just us five fighting the Iron Circle. This here's a letter from the clanfolk of Tor's Hold that they wanted you t'read and Reithann the Druid promised her aid as well. If Allbridge joins forces with the others in this vale, the Iron Circle will have an army t'contend with, not just a couple o'dusty adventurers.

"I s'ppose ye ne'er fo'ht a dragon afore? Stood oop t' a beastly foe tha'ud make most folk shite theer breeches? Weel dinna toss us off lightly friend, w're foightin' fer the loikes o' ye." Tafod seems a bit incredulous that and 'adventurer' worth their salt would be doubtful as to what might be accomplished by stalwart folk determined to right the wrongs of the Universe.

Dar takes the letter from Branna and reads it. Immediately he stands up taller and smiles. "Well, it seems you really do want to help! I'm sorry for that charade, but you have to admit that five armed strangers walking into my shop is somewhat suspicious." He waves the letter. "Branna tells me you helped get rid of those Toadwallow bastards. That's already quite helpful. Now listen up. If we’re going to beat the Iron Circle, we’ve got to draw Redthorn out of his keep. We need to get him angry. There’s a supply caravan heading out to Easthill tomorrow—you could rob it. If you left early tomorrow morning, you'd have time to set up an ambush on the road. Or you could leave now and spend the night in Easthill. Gods, just picking a fight with Iron Circle goons in any tavern in Harken wold would be a good start!”

Dar seems quite excited by the plan to rob the caravan. He takes out a large sheet of paper and starts drawing on it. "Now, the caravan will be expected to pass through Dardun, so you can't attack it until after that, or the Circle will know right away. After the river crossing, the land is too flat. That means the best place to set up the ambush is somewhere around between Dardun and the White River." On the crude map he's drawing, he circles that part of the road. "Actually, since most of you are not from Harkenwold, maybe you could use a more complete maps." Dar adds roads and settlements to his map, and hands it to you. "Hopefully this will be useful to you."

Map of Harkenwold:

Bram rubs his chin.  "Well... I suppose ambusing a caravan is as good a plan as any.  What are they transporting, anyway?  Where should we bring the goods back to?  Uh... can any of you drive a horse-cart?"  He scratches his head.  "Also... it would be helpful if we could resupply before we make that attempt.  I know I need more crossbow bolts.  And while I can hardly afford it, a rapier or other sword of some kind would be pretty helpful, too.  I'm sure everyone else has items they could use... anything to make this ambush have a greater chance of success!"

Dar fiddles with the pencil in his hand. "You know, that's a strange thing. I don't know what they're carrying. Could be they're sending reinforcements to Easthill, could be just supplies, could be something else. Whatever it is though, it's something the Circle wants and therefore something they shouldn't have. Once you find out what it is, you'll have to make your own decision as to what to do with it. The important part is that the Iron Circle finds out that they can't keep up this tyranny and expect to walk safely on our roads."

Dar listens to Bram talk about supplies. "If you're needing armour or weapons, Kathrid's smithy might have some. Tell her I sent you. Otherwise, White River Mercantile should have most other things you'd want."

Tafod will nod along as  Dar talks about an ambushcade. "Oy, bes seein' Kathrid then 'd bes a bright oidea, stock up onna few weepons, ammo 'n thet sort o' stuff.  Then we'd best hie t'ward Dardun, lest we bes ask'd questions Oi ponder it t' bes a good ooidea t' skirt round Dardun afor' we gits t' th' ambuscade site.  'ow long d' yer reckon it takes t' git to and round Dardun, say 'bouy 2, 3 moiles east o' thar?," he asks Dar

"The people on the caravan, are they members of the Iron Circle, or common folk being pressed to work for them?" Quyst  asks, a bit worried.

Dar nods. "Avoiding Dardun is a good idea. The Iron Circle has a strong hold on it. I reckon it would add an hour or two to go around, but the terrain's not too bad so you could do it without too much trouble. It would mean leaving very early tomorrow morning, but you it's probably worth it."

Answering Quyst's question, he says "Iron Circle don't trust Harkenwolders to guard their stuff. Anyone wearing the uniform is member of the Iron Circle for sure, they want to keep all the power for themselves and won't let any locals join up. Which is a good thing for us, in the end."

“I think we should go Kathrid’s a look.  I think I need to find something to hit from a distance.... don’t think I need to be running up on beasties from now on.  Didn’t work out very well.  Anyone else need anything?”

”I’ll start getting prepared for an early morning, yeah?”

(looking for any sort of crossbow or range weapon)

"I'd like to take a look at the stores, too"

Quyst is mostly looking around, but she might be interested in a finesse simple weapon, or some healing potions.

Ursula listens carefully to Dar Gremath and then gives a feral smile at the thought of ambushing an Iron Circle caravan. She studies the map and notes the relative distances between towns to build a mental map. She squints, judging the situation.

Lord Gremath, do you know anything more about what to expect from the caravan? How well-armed they might be, if they have any casters? Whatever you can tell us will be welcome.

Dar chuckles. "I'm no lord, little one. Most Circle caravans are guarded by three or four armed men, but the Circle does have mages among their ranks. It's best to be prepared for all possibilities."

Having concluded their business with Dar, the group goes to buy supplies for their ambush. Their first stop is the smithy. Kathrid is a black-haired, mature dwarf. She is working industriously when you come in, and continues to work as she greets you. Once you tell her that Dar sent you, she offers to sell you the weapons and armour for a reasonable price.
(You may buy any weapon and most armour at PHB prices.)

Quyst is not able to find any healing potions for sale in town.

Bram decides to buy himself an additional 22 crossbow bolts (1 gp, 10 cc) from the smithy, as well as a sling (1 sp), 40 sling bullets (something something copper), and a scimitar (25 gp).

Quyst doesn't find anything that catches her eyes. She's ready to follow the group in their next move.

Once they're ready for the next day, the group goes to the Mallard Inn to find somewhere to sleep for the night. The small tavern is occupied by a band of five human soldiers wearing black cloaks with a gray circle device. They are loudly harassing the taverner and the barmaid. Several other patrons— common Harkenwolders by their appearance—keep their heads down and try not to catch the soldiers’ notice.

“Now who the devil do you think you are?” one of the soldiers snarls when he sees you. “No one in this miserable town’s allowed to carry arms! Set ’em down if you know what’s good for you!”

Bram, seeing trouble brewing, turns to Quyst and Davner and whispers under his breath, „Tell ‚em we‘re here to join ‚em and maybe they won‘t pick a fight first.  We can still get the jump on them if they believe us. I‘ll help!“

If anyone tries to fool the soldiers, Bram will assist by standing behind them and looking dumb, dangerous, and imposing.

Quyst steps forward, saying firmly "We're here to join the Iron Circle. Can we discuss it with some of you, or should we look for someone higher in the ranks?" 

Deception check, with advantage: 21 (same for intimidation, if that matters)