Journey's Start

Ahead of the caravan...

Peony peers at the proffered juniper berries. "Yes....this is a good trade!" Smiling broadly, the pixie takes the juniper berries and then watches closely as Elowin gently and carefully extracts the berries from amidst the thorns. Elowin now has 10 glimmerberries. Each glimmerberry functions like a goodberry (as per the spell), but unlike goodberries, glimmerberries do not expire. Alternatively, Elowin knows that she can use six glimmerberries to reduce the cost of crafting a healing potion to one quarter the usual cost. Eager to show her haul, Elowin begins walking back to the meet the caravan.

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At that moment, in the caravan...

The grunt of some large beast sounds out from in front of Dugal's wagon, loud enough that even Morik hears it over the sound of the horses and wheels. "Uh...uh...guards? You'd better get up here - we've got a bit of a situation..." Hearing their employer's panicked voice, Adran, Bramlin, Gunter, Morik, and Princess all race forward as all the drivers pull their teams to a stop so as to not run into the lead vehicle. You see that the noise of caravan has awakened a creature that just emerged from a pile of leaves and is now looking somewhat out of sorts at the interruption. It's clearly deciding how to feel about this disturbance.I still need an initiative roll for Gunter. Each player can describe what they're doing as soon as they can post, and I will then resolve those actions in initiative order.

Initiative order:
Bramlin
Morik
Princess
Adran
Gunter
Owlbear

That is up to you and how you want to organize your PC. Typically javelins are carried in the hand, then plunked into the ground within easy reach for grabbing and throwing before a charging enemy can close to pike or sword range. As a soldier, Bramlin might be used to carrying them in his hands (one ready to throw, the others in his "off" hand), or bearing them as a bundle tied up with a cord, or having them within easy reach on a supply wagon. Or it could be that, as an adventurer, Bramlin has created any number of innovative ways to carry them independently from any supply train but which leaves his hands free: a really, really long quiver; or straps on the side of a pack. You're free to dictate what was the standard way that the military he served in prepared him for transporting his ranged weapons.

Ahead of the caravan...

Elowin steps out to await the arrival of the wagon train. But then she hears the bellow of a large, discombobulated woodland creature east down the trail...in the direction of the caravan! It might be a giant badger, a cave bear, a dire boar...or something even more dangerous!

In the caravan...

ROUND ONE (part 1)

Rushing up to the front of Dugal's wagon, the party sees the two horses rearing in their traces, whinnying in fear. A creature larger than any horse stands a few yards off the side of the road, shaking itself free of leaves that had collected on its slumbering form. It blinks large round eyes blearily, and gives another loud grunt as it tries to figure out what woke it. Morik and Princess exchange looks: they each recognize that this is a young adult owlbear, a deadly forest apex predator that could easily crush a person with a single blow or tear off a limb with a snap of its beak. This one doesn't look fully alert yet...

Bramlin's javelin sinks into the owlbear's flank (dealing the monster 8 piercing damage) and it roars in confused pain, whirling around to face its attacker, but its instinctive swipe only snaps the javelin in two. Morik plants his staff on the ground, and the power of the earth flows up into the weapon, swelling it and causing the whorls in the wood to sprout as knobs of incipient branches. Realizing that the opportunity for peacemaking is past, Princess sings a long, sweet, sustained note, and the area around the monster is filled with faeries flitting around, sprinkling a rosy glow on everything that doesn't dodge...including the owlbear (subsequent aimed attacks on the monster have ADV). Adran jogs up just as the owlbear spins around, still looking for its attacker. Seeing the rearing horses, it gives a roar of challenge and leaps forward at them. The first swipe of its claws snaps the neck of the horse, and the owlbear's beak tears out its throat. Dugal and Jalon leap down from the wagon and run past you; Gavath wails in anguish from nearby.

None of the party members are in melee range of the monster, but everyone except Elowin is within one move of it so you can close for a melee attack or back away to keep your distance without fear of providing the owlbear an opportunity to attack.

To finish round one, we need the following:
@JoshuaMabry We need another crossbow attack roll for Gunter, representing the ADV that Princess' faerie fire gives him. DONE.
@MaJunior We need a turn for Adran. Because the owlbear is waking up from hibernation, Adran will act before the owlbear with the rest of the party. DONE.
@grifter730 We need Morik's action for the round, now that he realizes about owlbears and that the party is in a fight now. DONE.
@runekyndig It will take five move actions for Elowin to rejoin the caravan; you can decide what combination of moves, dashes, and other actions you wish to take.

Edit: I've struck out the text of what didn't happen, because Morik's Entangle spell prevented the owlbear's attack this first round.

ROUND ONE (part 2)

Bramlin started the battle, hitting the owlbear for 8 piercing damage!
Morik cast shillelagh and then, realizing the gravity of the situation, Entangle. The leaves exploded into the air as thick ivy burst from the ground like an octopus' tentacles, seeking to wrap up the monster and hold it in place. The vines wrap around and around the large monster, restraining it and preventing it from attacking its opponent...the horses drawing Dugal's wagon!
Princess sang out Faerie Fire, which limned the shaggy monster with a pink glow that draws the eye.
Adran powered a dagger into its haunch, dealing the monster 5 piercing damage!
Elowin hears the commotion and considers how she can help.
Gunter aims for the monster, but then, as Princess' vocals evoke the faerie magic, he adjusts his aim to target the pink glow and sinks a crossbow bolt into its belly, dealing the monster 2 more piercing damage!
On its turn, still waking up, the owlbear attempts to break free of the grasping vines...and is unable to escape!

Please, submit your actions for round two; I already have Bramlin's round two attack. We begin the round with the owlbear restrained at a distance of about 40' from the PCs.

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Bramlin (13/13)
Morik (13/13)
Princess (9/9)
Adran (10/10)
Elowin (10/10)
Gunter (10/10)
Owlbear (?)