Setting up the table for our first D&D session had me feeling quite a mixture of emotions. Firstly, I was super-excited to finally be doing playing the game with a group of friends. Secondly, there was definitely an ample amount of nervousness and anxiety that came with the fact that I was responsible for telling the story, describing everything the characters saw, heard, felt, smelled, etc.
After sitting down in the DM chair at the head of the table I took a deep breath. “What did I get myself into,” I asked myself aloud.
Turns out, a lot of friggin’ fun!
Our player’s characters (from here on out referred to as PCs) are contracted by a dwarf named Gundren Rockseeker to escort a cart of mining provisions from the city of Neverwinter to a trading post in the town of Phandalin. He’s found “something big”, and needs the goods delivered there post-haste. He goes on ahead of the PCs with a warrior escort named Sildar Hallwinter to “take care of business” in Phandalin before the PCs arrive.
Being the over-prepper I found myself turning out to be when it comes to being a DM, I queued up the sound I had on my iPad for a cart being pulled by oxen. (Yes, that exists in Spotify!”
Even though we went forward with the idea that they all somewhat know of one-another in accepting this job, I asked our PCs to introduce themselves to the table. Miles unveiled his dwarven barbarian’s accent too much laughing and snickering from the table, and Adam’s mysterious half-elven ranger’s introduction consisted of “I’m Wil.” It seems like the other PCs will have to tease more out of him if they want to know more.
A few days of travel on the trail had Rich’s character Maran driving the cart, Miles’ character Magnus “had a rough night” and was trying to sleep in the back of the cart among the shovels, pickaxes, and bags and barrels of supplies. They came upon a grisly scene blocking the path when they found two dead horses, riddled with black-tipped arrows, that they recognized as Gundren’s and Sildar’s horses.
Our heroes stopped the wagon, and went on high alert. This wasn’t good.
Erik’s Paladin Agnar moved forward to investigate the scene, and from the woods heard a Goblin yell, “NOW!”
Roll. For. Initiative.
For me, watching the player’s strategize this battle (and ensuing ones) was one of the best parts of the night. With some rough rolls from me, the goblins didn’t surprise the PCs, but suddenly five of them poured out of the woods near the horses, with three charging Agnar and two hanging back to pelt the characters with arrows. Corey’s rogue Draxan managed to peel off into the woods, moving around to flank the goblins.
However, their ambush did not go as planned. A well-timed entangle spell from Louis’ druid Tuck managed to catch a pair of the front-line goblins in a mess of vines that grew from the ground and wound their way up to restrain the goblins. The third was able to pull free in time to jump back. (Being restrained gives enemies advantage to hit (they roll their 20-sided attack die twice and take the higher of the numbers and gives you disadvantage on your own attacks where you roll it twice and take the lower of the totals).
Agnar is hard to hit normally (though he did get tagged by the goblin leader early), but with disadvantage on attacks the goblins only managed to bash their scimitars off of his shield and armor, with no hits taking purchase after the vines were in play. Wil fired his longbow from the rear lines and felled a goblin archer with one hit to the heart. Slowly but surely, the tide of battle was shifting towards the PCs. Goblin archer #2 took an arrow to the shoulder and abandoned the field and rushed into the underbrush and our final goblin fighter was slain, giving our adventurers their first victory!
Investigating the area revealed that this area had been used for goblin ambushes for quite a while, and Wil’s ranger tracking skills noticed a trail where the retreating goblin ran, finding tracks of about a dozen of the creatures as well as marks that looked like two larger creatures were dragged from the road. Our players deduced that Gundren and Sildar were captured and decided to hide the wagon and its goods and follow the goblin trail.
Goblins are tricksy folk, but Wil and Draxan lead the group in proceeding cautiously, uncovering and avoiding both a snare trap and a pit trap on the trail following the tracks. They follow the trail for about five miles and come to a clearing where the trail leads into a cave with a stream flowing out. As they approach, they come upon a clearing and surprise four goblins (the escapee from the earlier fight telling the tale of their clan member’s demise) and manage to surprise them and dispatch all but the injured party whom they interrogate for information. They learn that the leader of the cave, Klarg, is a bugbear who answers to the goblin King, Grol. Gundren and Sildar were kidnapped on the order of The Black Spider. Sildar is inside the cave, and Gundren was taken to Cragmaw Castle along with his map.
Our heroes decide they need to rescue Sildar so enter the cave on the sly. Creeping up into it, they find three wolves chained up in a room and decide they aren’t a threat and keep going forward into the cave. (The wolves eventually are agitated by the intruders, and two of the three break free from their chains and attack). After dealing with the wolf threat, Magnus the Barbarian manages to scramble up a 30′ rock face and feed a rope down to bring up his compatriots.

Within the chamber they’ve scrambled into, they spy two goblins, a wolf, and the bugbear, Klarg. Yet again, they’ve gotten the drop on their enemies since apparently I can’t roll good perception for the monsters to save my life. What ensues is a full surprise round for the adventurers, and they lay waste to the not-so-mighty-when-surprised Klarg and his allies.
They find his hidden treasure chest among crates and barrels of stolen provisions and end up with some bling in the form of copper pieces, silver pieces, some healing potions and a small jade statue of a frog.
That’s where we wrapped it up for the evening.
As I wrote in the last entry, I wanted to get into D&D so that I could roll a character and be a player, but I (a bit begrudgingly) decided that if I wanted to play with my friends, I’d have to take up the mantle of DM.
It was WAY more fun that I had anticipated!
Some of my favorite takeaways was seeing the guys actually get into their characters. Trying voices, (sometimes to great comedic effect), thinking like their character would and making in-game decisions based on that, (even if it led to contradiction when one character questioned and let the goblin go, and as the goblin moved to escape, another slew him where he stood), and the various in-game zings sent each-others way over a roll, or something said, etc.
I can’t wait to see what happens next and how the guys get even further into their characters and I’m glad you’ll be along for the ride!