Entrusted with the task of investigating the news of the lost Dwarven city, the party heads out. The weather is fair and sunny as you trek up slopes and through woods. As you get closer to the site you start seeing evidence of humanoid habitation here and thing. Chopped down trees. Hunting snares. Humanoid tracks. Eventually in the woods you see a clearing in the distance. Though the foliage immediately around you is thick you can see some goblins and hobgoblins ahead. One of the hobgoblins, dressed in half-plate, seems a fair bit tougher than the others.

What do you do?

Battlemap with positions

Areas shaded in green are thick enough to be rough terrain for the purpose of movement. And provide 3/4 cover for creatures in them. Shooting out of the green-shade also gives 1/2 cover to creatures out of it.

And if there's anything your characters would've done while coming to the location, please feel free to mention that.

Way There:

Dain struts along the path, making small talk with the group he's about to go excavating with. He's affable the whole time, but gives the general impression that he thinks his past military experience puts him in charge. As a result, he tends to walk in the front of the group until they get to the battle map. He wears simple but efficient boots and pants, with a tied-up shirt that looks ready to tear on the knotted muscle beneath. His trusty axe is slung over his shoulder and fastened by a harness. He boasts about having once felled a manticore with it.

At Map:

Dain puts his hands on his hips and examines the situation from a distance, waiting for everyone to catch up the few feet ahead he was. "Some goblins making camp here. What do ya' think lads? Should we march in and talk or say they're ill-tempered and cut right to the fun part? I don't want to start a fight if we can just walk by, but I'd love ter wrestle the tough guy up front if we need it."

Either way, he slows down so as to not make much noise as they approach.

In explaining his strengths and abilities to his teammates when heading out, Finn would have summoned his oversized longsword (functionally a greatsword in his rather small hands) and would have kept it out, leaning the blunt side of it on his shoulder as they continued walking. He would also have been quite friendly towards Dain, to try to ingratiate himself to the obviously-tough dwarf.

At Map

Upon spotting the goblins, Finn stopped, and began quietly chanting a spell to curse the apparent leader as he readied his blade. He then turned to the others. "Should I fly in from above to distract them?" he whispered, eyes alight with mischief. "If we plan this out, we can beat them before they even know what's going on!"

Finn will cast Hex on the half-plate-clad captain, who's just within range, and will target his Strength to give disadvantage on Ability checks. He'll use a 3rd-level spell slot to do so.

(( Most of my DMs have treated the spell as if it didn't really have visible effects; but if it's going to be visible here, or if it would in any way tip off the goblins or announce our presence, he'll refrain from casting it and just whisper to the others instead. ))

Sampson confidently travels with the group but makes sure to slow down for anyone that might be trailing behind. He listens to everyone’s stories and chuckles as Finn summons a sword too big for him.
Anyone who would inquire would quickly know that Sampson commonly goes by Sam. 

As the group approaches the apparent goblin infestation, Sam listens to the ideas from the group and supports the ideas of an attempted surprise approach. When the party decides on the course of action, Sam will chant a prayer softly and cast Bless on Finn, Dain, and himself! 

(Finn and Dain, you now have an additional 1d4 to add to your attack rolls and saving throws! I’ll try to remember to remind you if you forget.)

@Rod, I'd treat Hex as a cause to roll initiative. The spell itself being invisible and having no outward signs on the hexed target seems A-OK in my book. But with it having offensive capabilities and a hexed ability, I'd say the target would know something happened to them.

@Lil50Sampson's Bless is noted.

@All, forgot one detail to describe that I probably should've mentioned. (Brain fart on my end.) Behind the goblins the mountain slopes rises steeply and they stand before a stone entrance.

Quote from VitusW >>

@Rod, I'd treat Hex as a cause to roll initiative. The spell itself being invisible and having no outward signs on the hexed target seems A-OK in my book. But with it having offensive capabilities and a hexed ability, I'd say the target would know something happened to them.

(( Cool; no spell, then. ))

En Route:

For most of the journey, Psalm has spent more time listening than talking. He's done his level best to lavish each member with just the right amount praise. He encourages Dain to regale the group with stories of his noble military service. He marvels at Finn's mystical weapon. He asks Sampson about his faith, listening with an eager ear that would suggest he's a potential convert. 

Throughout it all, he makes faint allusions to his past heroics... some business with a blue dragon... single-handedly facing a shadow demon... but he waves it all off as being nothing of great significance. He quickly redirects the conversation to zealous but genuine interest in whoever he's talking to.

At the Map:

A wide smile crosses Psalm's face as he sees the goblins in the distance.

He rubs his hands together as he whispers to the others, "Well, a fight is always fine thing, but it's never quite as fun as pulling one over on a group of dopes who pulled the short straw on guard duty."

He looks to Finn, "Flying above would be a fine distraction... However, it might draw an immediate attack. I might be able to buy us a slightly more time to move into position with just a bit of verbal razzle dazzle. Or I could envelop them all in darkness, allow us to move into position, then drop the darkness so we can play. Either way, the look of astonishment on their faces will be worth the entire journey up here."

Quote from MAOShea >>

"Flying above would be a fine distraction... However, it might draw an immediate attack. I might be able to buy us a slightly more time to move into position with just a bit of verbal razzle dazzle. Or I could envelop them all in darkness, allow us to move into position, then drop the darkness so we can play. Either way, the look of astonishment on their faces will be worth the entire journey up here."

Finn smiled devilishly at the tiefling. "I like your style!" he whispered back. "My patron's fond of the dark; he'd approve of that plan especially." The warlock pirate looked towards the others to see what they thought.

"If they're standing guard over the path, there's only one way we're getting things done. Just tell us where to position for this plan o' yours."

Sampson listens to the group plan and agrees to the use of darkness.

”Though darkness doesn’t seem to last long around me, I know it can be useful. I’ll try to stay close to everyone in case of emergency!” Sampson ends with a supportive nod.

He holds his walking stick out and chants quietly in Sylvan. A warm greenish light spreads across the wood and then fades away. 
(Casts shillelagh on his quaterstaff) 

En Route:

Zylborin is a collector of tales, he loves to hear of the tall kind, the non-fiction, and everything in between. On the journey to the Barrier Mountains the Bard would sometimes regale the other travellers with his songs and epics. But most of the time he would be listening to any tales the fellow travellers would be kind enough to share. He quite enjoyed the tales of the Pirate and the Tiefling fellow, not to mention the adventures of the Half-Elf and Dwarf.

Gates:

Zylborin quietly moves up to the group, "Sorry, I fell a bit behind back there. I heard most of the plan, I can turn one of you invisible as well if that helps?" He pulls over his shoulder his Cittern and absentmindedly begins to turn one of the tuning pegs.

"Well then..." Psalm says. "Let's have some fun, shall we?"

And with that he sneaks forward until he's close enough to to envelop all of the orcs in Darkness

(I assume this triggers initiative, but if it doesn't there's more he'd love to do.)

Sampson follows closely behind as this happens. He will ready himself to hurl a handful of flame at one of the enemies if they are within 30ft!

As the group gets into position, Dain draws his axe and moves as close to the edge of the treeline as he can without being spotted, waiting for the signal that is Darkness to strike.

Still grinning like a cat, Finn activated his boots and levitated a few inches above the ground, then began quietly gliding forward until he was only 15 feet inside the treeline. He then waited for Psalm.

As Psalm casts darkness the goblins get up from their inattentive position and ready for battle, startled by the sudden blackness surrounding them.

PC Init
Psalm: 22
Sampson: 18
Finn: 18
Dain: 3
Zylborin: 18

Goblins Initiative
G1: 12
G2: 6
G3: 22
G4: 12

Hobgoblins Initiative
H1: 6
H2: 3

Captain Initiative
Cap: 7

Quote from VitusW >>

As Psalm casts darkness the goblins get up from their inattentive position and ready for battle, startled by the sudden blackness surrounding them.

PC Init
Psalm: 17
Sampson: 15
Finn: 10
Dain: 7
Zylborin: 11

Goblins Initiative
G1: 10
G2: 21
G3: 3
G4: 14

Hobgoblins Initiative
H1: 17
H2: 3

Captain Initiative
Cap: 5

Working out the Init Order

Initiative Order

G2
Psalm, Sampson
H1, G4
Zylborin, Finn, Dain
G1, Cap, G3, H2

After Psalm's darkness descends, one of the goblins (G2) is the first to act. He runs out of the darkness seeking who struck, and lets loose arrows from his shortbow at the approaching party.

Target numbers: 1: Dain, 2: Sampson, 3: Finn, 4: Psalm

Arrow 1
Target: 2
Attack: 11 Damage: 5

Arrow 2
Target: 1
Attack: 12 Damage: 6

After loosing his arrows he ducks towards a nearby tree in attempt to hide his location.

Stealth: 20

Map

Black-circle area is Psalm's Darkness. Have the goblin behind the tree as your characters would know where he ducked for cover. Just apply your passive perception against his stealth (and or line of sight from positioning) for determining if you can see him.

Initiative

Psalm, Sampson <---------- currently up
H1, G4
Zylborin, Finn, Dain
G1, Cap, G3, H2, G2

//swapped G2 down to the bottom with the other goblins/hobgoblins as that whole group will be going together from here on out

Psalm, giggling, moves forward 15', ducks behind a tree and knocks an arrow, ready to loose it at the first creature to step out of the sphere of darkness...

Sampson moves forward with Psalm, readying himself for the fight ahead! He fumbles through the grass and manages to notice the goblin that darted out of the darkness (Passive Perception 17). He points his finger and chants in Celestial. The sound of a great ominous bell fills the air around its head! 
(Goblin 2 will need to make a DC 16 wisdom saving throw or take 9 necrotic damage)

G2 WIS Save: 11