In the city of Neverwinter, a dwarf named Gundren Rockseeker asked you to bring a wagonload of provisions to the rough-and-tumble settlement of Orlane, a couple of days’ travel southeast of the city. Gundren was clearly excited and more than a little secretive about his reasons for the trip, saying only that he and his brothers had found “something big,” and that he’d pay you ten gold pieces each for escorting his supplies safely to Barthen’s Provisions, a trading post in Orlane. He then set out ahead of you on horse, along with a warrior escort named Sildar Hallwinter, claiming he needed to arrive early to “take care of business.”

You’ve spent the last few days following the High Road south from Neverwinter, and you’ve just recently veered east along the Triboar Trail. You’ve encountered no trouble so far, but this territory can be dangerous. Bandits and outlaws have been known to lurk along the trail.

Introduce your character! Describe their appearance and mannerisms.

What is your marching order? Who’s in front, and who’s bringing up the rear? One or two characters need to be driving the wagon of Gundren's supplies. The rest of the characters can be riding on the wagon, walking alongside, or scouting ahead, as they like.

Ronald "Big Bear" Foster is a tall, broad-shouldered half-orc man. His short brown hair is streaked with some grey and there are some small creases on his face, hinting at some life lived. His arms are covered in hair, along with the small bit of chest peeking through his red shirt.
He carries himself with a comfortable posture, and a warm demeanor. Whilst not super talkative, he enjoys listening to his fellow travelers and is genuinely interested in who they are. He talks to the horses on the road, and laughs off any suggestions that he can actually talk to animals.

I see him as being one of the characters driving the wagon, but if other characters would rather drive, he's more than happy to walk along to give up his seat to another (he Does have land vehicle proficiency)

"Doc" Jennings is a deceivingly thin man with a receding gray hairline, widow's peak hairstyle, no facial hair and thick glasses. Dressed in a long dark leather coat with a simple chest piece beneath, his attire is hardly a Around his early fifties and at a glance, he might make others question why he would even be traveling the roads, let alone as part of a caravan guard. Despite this, he walks with seemingly perfect composure and will have spoken at length with anyone interested in anatomy, biology or the sorry state of the medicinal arts of this day and age. With having been on the road together a while, one might even consider him to be long-winded. Though his humor tends to be on the morbid side, one can tell easily that this old gray fox has a spring in his step and a bright, hopeful demeanor.

He would be taking turns either driving or walking. Walking to the eastern side will be his preferred position.

Yed Orilo is pale, sinewy, young Goliath who is shockingly polite whenever around anyone. Yed is dressed in poor leathers and fabrics that look the role of being found clothes, used only in desperation. He looks every bit the role of a man hired just for his height, the apparent inherent fierceness of his race, and the look of pity Gundren can’t help but hide when speaking to Yed. He has long dreadlocked black hair, with bright blue eyes that always seem to be looking at the floor. The only thing standing out among his apparel is a single, bright blue feather earring hanging from his left ear. He doesn’t speak unless spoken to. But when he does he speaks with a cadence and tone that would seem at home with people of higher social standing than those that one would expect when guarding a caravan. Yed almost seems to be slouching most of the time, as if used to making himself seem smaller a threat. He carries a large, and almost gaudy silver warhammer with a head forged to look like that of an eagle. 
     Oddly enough Yed has managed to get along somewhat with the strange Doc Jennings, enjoying his educated discussion. Though instead of the sciences Yed loves discussing...art. Yed has been walking the most of trip, perhaps scouting ahead every once in awhile to make sure we’re all safe. 

Shamash Turnuroth towers over most people he is near, but somehow doesn't seem to notice it. On the journey so far, he has mostly remained silent, listening to those around him. Periodically, perceptive companions might notice him figiting nervously with the red cords tied around his wrists. So far, when he has joined in the coversation, it has displayed an obliviousness indicative of inexperience. His silverly blue scales are rigid, making it hard to read him. But whenever he speaks, he seems friendly enough. He laughs quickly at other people's jokes, but usually a few seconds after the punchline. He walks with a steadiness of someone who is musclebound and athletic, but somehow doesn't seem to fill the space around him. 

Shamash has stayed near the cart for the most part. He was raised in a city and it shows. He is slightly out of his element in the wild outdoors, and really wants to make sure he does this job right. 

Ena Umequinal's petite frame does nothing to take away from her flamboyant appearance. She wears a purple cloak with a gold-rimmed white undershirt and pointed boots, and her pointed hat, which is embedded with an array of gold and purple jewels, casts a thin shadow over her long light-ginger hair and amber eyes. Her personality is as expressive as her clothes; she speaks eccentrically, and often changes from cheerfully making casual conversation to speaking in dark, mysterious, and decidedly smug undertones. She consistently finds ways to weave the discussion from various topics on arts and sciences and into magic, myths, and the occult, expressing mastery in her knowledge of such things regardless of whether or not it's relevant. Ena seems eager to greet her fellow travelers, but she is rarely the first to express her thoughts, betraying a hint of shyness. Whenever conversation dies, she performs monologues with her pet black cat, which wears a tiny hat to match her own. She seems to treat the cat as though it were communicating back to her, but who knows if it's really saying anything?

Ena positions herself near the center of the wagon, where she can draw a decent amount of attention and comfortably join the conversation without having to exert herself walking or struggle to greet the others. She never shows any desire or intention to walk alongside the wagon or to drive it, and she silently respects those who show what she views as tremendous feats of strength and skill.

Yed hummed along to an old lullaby he’d never quite managed to get out of his head. A few steps away from the caravan, he’d begun to take in the rather pleasant weather they’d been experiencing traveling down the Triboar Trail. He inspected his nails nervously as he looked around, this was just supposed to be a normal escort job for Gundren. His heart began to beat quicker at the thought of running into bandits, he hopes this will be a quiet trip. 
  “You’ve gone too long without a proper wash Yed, what would Lord Henry think?” Yed muttered quietly to himself as he continued his path scouting a couple of paces past the caravan, eyes alert for potential threats.

Big Bear listened as Ena and Doc turned conversations through twists and turns like master pilots, keeping an eye on Yed who seemed uncomfortable in his settings. He motions for Shamash, who looks like he’d rather be riding on the cart to sit up on the driver’s bench beside him.

You’ve been on the Triboar Trail for about half a day. As you come around a bend, you spot two dead horses sprawled about fifty feet ahead of you, blocking the path. Each has several black-feathered arrows sticking out of it. The woods press close to the trail here, with a steep embankment and dense thickets on either side. The pair of oxen pulling your cart snort and stop in their tracks, avoiding the dead beasts.

Spotting this first, Yed pulls his Warhammer from his back with great apprehension. Going back enough to not have to shout to Big Bear. Whispering almost to the point that even Big Bear can’t hear him,

”Big Bear! Two dead horse ahead, struck by several arrows. Should I go try and move them aside?” Frantically whispered Yed as he turned several times during the conversation to look both at Big Bear, and the obstruction ahead. 

“It must be the work of bandits, only people like that would hurt horses with no regard” muttered Yed absentmindedly as his brow creased in worry looking at their surroundings.

Ena's incessant chatter comes to a close when she spots the carcasses. Her cat gazes indifferently at the grizzly scene as Ena's expression twists from indulgent to concerned. She grips her staff and warily searches the faces of her comrades, resisting the urge to continue staring at the blood that was pooling thickly around the animals. "I wonder what happened here..." She frowns, then suddenly stands, making a show of bravado in order to stop herself from acting helpless. "Be on the lookout! Danger lurks within this trail, I can sense it." She smiles and confidently brandishes an embellished, suspicious-looking tome. "There's no need to be afraid; any attackers will soon perish from the full might of a demon lord from the deepest depths of the Abyss."

Greatful to have a place by Big Bear, Shamash had calmed notably over the last stretch, but as soon as he hears Yed and Ena he snaps to attention, the muscles taut and ready to burst. 

"It is senseless to kill the horses. Some poor soul must have met a grisly end here." Shamash quiet touches the cords around wrist and says a quick prayer to Ilmater.

"Weren't Gundren and that Sildar individual supposed to be riding ahead of us?"
Doc pondered aloud, scanning the treeline for any hint of bandit presence.

As Doc looks around, he hears a whistling noise as an arrow whips past him. It's an ambush!

Two goblins jump down from the enbankment and rush towards the cart with drawn swords. As arrows shoot through the foliage towards you, you can see two other goblins with bows.

The ones with swords slash at Doc Jennings while the arrows are aimed at Yed.

1st Scimitar Attack: 24 Damage: 10
2nd Scimitar Attack: 21 Damage: 8
1st Shortbow Attack: 16 Damage: 6
2nd Shortbow Attack: 20 Damage: 8

The melee goblins then disengage and scurry out of the reach of your weapons. The archers disappear into the foliage after releasing their volley.

Initiative:

Goblins: 3
Yed Orilo: 4
Doc Jennings: 7
Ena Umequinal: 23
Ronald Foster: 3
Shamash Turnoroth: 10

The goblins act again!

Big Bear leans over to Yed, keeping his voice just loud enough for Shamash and Ena to hear
"Stay close to the cart, but stay low and ready for trouble. Shamash, keep watch on the tree line. Ena, keep up the eldritch pomp and circumstance, it might make us look like too much trouble in case any bandits are thinking about attacking us."

Big Bear tries to get Doc's attention by waving his hand very lightly.
"Doc. Doc. can you get closer to the horse, and check to see if there are any signs of where the riders are or what happened to them?"
Big Bear tries to calm the Oxen on the cart to get them to slowly approach the horses
23 Animal handling

Profiting from the confusion on the cart, the goblins pounce back again and two more arrows shoot down from the trees.

The arrows target Yed again, the scimitar-wielding will attack Doc until he's unconscious, then they'll switch their attention to Big Bear.

1st Scimitar Attack: 9 Damage: 3 
2nd Scimitar Attack: 6 Damage: 3 
1st Shortbow Attack: 21 Damage: 4  
2nd Shortbow Attack: 22 Damage: 4  
REAL Damage Rolls: 1S: 3 2S: 8 1B: 4 2B: 7

The first goblin strikes the pommel of its scimitar hard into Doc's chin, and he goes limp. The second slashes at Big Bear before the pair retreat again.

Big Bear, seeing Doc get cut down is going to spring into action. With a shout, Big Bear is going to leap off the cart and run towards Doc. After whispering some soft words while moving his hand over the end of his carved walking staff, he will place his palm on Doc and cast Cure Wounds 6 . He'll take a bonus action to then channel some power into some smooth river stones from his pocket, casting Magic Stone.

EDIT: Big Bear then places a smooth, vibrating stone into Doc's hand and whispers

You ready for some payback?

Seeing that BIg Bear has already seen to Doc, Shamash strides after the goblins with his shield and longsword at the ready. He will follow the melee goblins on the most direct path possible. As soon as he gets to the nearest one, he makes an attack with his longsword.

Attack: 13 Damage: 5

If possible, Shamash will shift around without leave melee range to position him between the goblins and Doc.

Shamash manoeuvres into a favourable position, but the goblin ducks under his sword as he strikes. 

Regaining his composure after the goblin stole his consciousness and Bear brought him back, Doc shakes his head and removes the shortbow from his shoulder. He looks to his rescuer and notches an arrow, aiming at the goblin that struck him that appears engaged with Shamash!

”I appreciate the assistance. I’m not accustomed to being the patient.”
Attack: 10 Damage: 16
"Payback though? Yes. That seems reasonable."