If I had advantage 9

Randall:

As he sits calmly praying to be granted the new spell he needs to communicate with the natives, Randall cracks one eye open to see the friendly method his companions are using to make first contact—great big hugs from overly-friendly shrubbery and gentle pats on the face by their flying monk—then cracks open the other eye noticing the rim of the huge pit nearby, still unexplored and potentially filled with deadly menace.

“Ah, well, such is the life of an adventurer,” he thinks and smiled wryly, returning his focus to his prayers.

I think it’s right about then that Petcan peers down into the hole, feeling drawn towards the dark. He’ll cast dancing lights and send a figure of light down into the hole

Now is with Randall practising on a tree, after he did a quick investigation of the pit: 9

You miss the struggling native and he tries again to escape.

STR: 6 

The hole is dark and deep. The dancing figure illuminates what appears to be a bottomless pit, or at least very, very deep.

The native frees himself, sheathes his axe, and runs off after his fellow tribesmen.

Has Z's little Imp found the village? Or whatever place the path leads to? Perhaps we can try again and engage with the natives. Randall can cast Tongues, and then we may be able to find out what is going on. E.g. why the villagers were not being attacked, and why they were playing the instruments. Z assumes that the two are related, but one can never be certain.

Also, just for good measure, Z will cast "detect magic" around the site in case he finds anything interesting. (Since level-up, Z can now do this as at will as a cantrip without using spell slots)

This is near the end of the 3rd day. If you want Irraxan to continue following the path, he does, but so far it just continues in the direction you were traveling.

Dismissing the spell Tempe alites on the ground and waits for the others watching towards the natives pass. Then continues with his group. If they want too. 

Randall:

Finishing his prayers, Randall moves over to the pit carefully, checking in with Petcan, "Did you find anything useful?  If needed, I can summon a more powerful light to investigate further."

Curious himself, Randall casts daylight on the plant corpse closest to the pit and kicks it down into the abyss below.

“That’s one way to do it.” Petcan huffs a laugh. 

The Purplewrath's illuminated corpse falls and falls, occasionally hitting against the sides of the hole, before finally coming to a stop what must be more than a thousand feet deep.

Tempe walks back to the group, "I tried to catch one, but sadly failed." He smiles "Maybe, I can be too intimidating? I should work on my social skills."

This ends the 3rd day. Post your preparations and watch order for your long rest. Near the end of tomorrow you will reach the site of the bonfire blaze.

Does Irraxan keep following the foot path long into the night, or return after some length of time?

Randall:

Backing away from the pit, Randall says, "I see no need to investigate this pit further today, though we should make sure to mark its location on our map."

Looking around, he asks, "Is anyone injured?  I can provide magical healing before we set off or just bandage you up while we rest a few moments.  I suppose we should follow the path of the natives afterwards and attempt more...calm...negotiations."

“I don’t know that it’s safe to stay right here next to the hole.” 

Bow is fine taking the first watch, and is also fine with being near the hole; or not near the hole.

Zenodor ask Irraxan to return to the camp and allows him to take a rest along with the rest of the party.

While we are gathered around the campfire, Z strikes up a discussion with the rest of the group about their next steps. He suggests that there are two paths open:

1. Explore the hole. Too deep for ropes, but Z can cast Fly on 2 targets, and has a magical item that lets him fly without a spell. So that covers 3 of the party. Can someone else also cast something similar? We could then explore the bottom of the pit. If we do this, it may be wise to send Irraxan down ahead of us. A hole over thousand feet deep certainly seems unusual, given that we are on a small island where ground water should normally be not too far below the surface. Perhaps a den of some sort of monster? Or perhaps an entrance into the Underdark? Either way, it sounds like something that may affect the safety of the trade settlement we are trying to help establish here.

2. Ignore the hole, follow the path which in any case seems to be going towards where we were heading. This seems to suggest that maybe the village (or whatever) these villagers came from, and the distant smoke we observed days ago may in fact be the same location. We can always do 2 after 1 if there is nothing interesting at the bottom.

Z votes for option 1 (explore the deep hole) but is happy to pursue #2 if the group prefers.

Bow would like to do both, but thinks talking to the natives first is more important at this point it time, and they might have information regarding the hole as well.

Randall:

"I can heal anyone who was injured, though I have no means to magically descend safely into the pit," replies Randall, moving well away from the pit before setting up to rest.