Encounter of the Week: Detour Past Dragonspear

The Road to Baldur’s Gate has led your party to the ancient, blood-soaked fields surrounding Castle Dragonspear. The road disappears into wilderness here, and it won’t reappear again until they reach the settlement at Boareskyr Bridge, some 100 miles distant. The adventurers must make a choice of which route to take through the wilderness.

This week’s encounter is titled Detour Past Dragonspear, in which the characters must successfully navigate through the wilderness around Dragonspear Castle. This encounter is part of the series “The Road to Baldur’s Gate,” in which a group of adventurers will travel down the Sword Coast for nearly two months over road and wilderness, from the gates of Waterdeep to the threshold of Baldur’s Gate. You may use this series as an introduction to the upcoming D&D storyline Baldur’s Gate: Descent into Avernus, as an expansion to the caravan sequence in the first D&D storyline adventure, Hoard of the Dragon Queen, or piecemeal as standalone encounters.

You can keep track of this journey on this massive map of the Sword Coast, originally presented in the Sword Coast Adventurer’s Guide. The trip from Waterdeep to Baldur’s Gate covers about 750 miles of both road and off-road wilderness. A small party on horseback can cover about 24 miles per day at a casual pace, with just under two days off for rest per tenday of travel. All in all, this journey takes just over a month to complete for a small party of adventurers—assuming they’re well-prepared and no serious complications arise. And note, not every day of travel needs to be represented by an encounter; the characters may go for days with only minor encounters with passing merchants or travelers.

This is the fifth encounter along this journey. The previous encounters are:

  1. The Road to Baldur’s Gate
  2. Devil in the Details
  3. Danger in Daggerford
  4. Misty Marauders

Leveling Advice

Though this encounter series is supposed to lead directly into Baldur’s Gate: Descent into Avernus, that adventure begins its characters at 1st level. You can choose one of the following options, or create your own plan, in order to make this series flow smoothly into Descent into Avernus:

  1. Treat this series as a prologue, and start Descent into Avernus fresh at 1st level with new characters
  2. Scale up the Baldur's Gate content in Descent into Avernus from 1st to 3rd level, and slow XP gain down significantly by halving or even quartering XP values until they reach Avernus.
  3. Skip the Baldur's Gate content and go straight to Avernus.

Exploration Encounter: Detour Past Dragonspear

This skill challenge is suitable for characters of 2nd level. Success on this skill challenge will result in the characters finding a safe path through the wilderness, while failure will lead them astray.

In this encounter, the characters must use their wits to find a way through the wilderness and avoid monsters. This period of exploration and pathfinding is represented by a skill challenge, a type of encounter derived from an earlier edition of D&D that challenges the characters outside of combat. It also gives the players a chance to describe the story of their travels themselves.

 If the characters succeed on this skill challenge, they make it through the wilderness safely, and may even find some treasure. If they fail, they find themselves in a dangerous situation. In addition to succeeding or failing overall, each successful or failed ability check within this skill challenge could lead to danger or rewards.

Encounter Start

As the characters reach the end of the road, read or paraphrase the following:

You stand at the end of the Trade Way. Here marks the lands in which civilization has been washed away by the tide of lawless monsters—and nothing makes this threshold clearer than the Trade Way itself. After traveling about 350 miles of road over the course of a tenday and half, the well-trod dirt of the road dissolves into untamed wilderness. A sea of tall grass spreads out before you, and looming over all of it is the silhouette of a once-mighty castle standing upon a hill. An aura of ancient danger surrounds this place.

Here, the characters are faced with a choice. Which way to go?

  • To the east are the ruins of Dragonspear Castle, a nasty shell of a fortress brimming with hobgoblins and other unpleasant creatures.
  • To the southeast are the open fields surrounding Dragonspear, a grim wasteland littered with the ancient remains of long-dead warriors, and populated by monstrous scavengers.
  • To the south are the foothills of the Trollclaws, a dangerous region of hills inhabited by monstrous trolls.

Perhaps the characters will consult their maps, or perhaps they will survey the surrounding landscape. In either case, once they’ve chosen a direction, their skill challenge begins. They must use all of their wits and wilderness survival skills in order to make it through safely.

Skill Challenge: Navigating the Dragonspear Wilds

In this skill challenge, the characters try to avoid monsters and make it through the Dragonspear Wilds and to Boareskyr Bridge as quickly possible. In this skill challenge, each character’s turn lasts 14 hours of in-game time—that is, each turn is one full day of travel, once you account for packing up gear, unpacking gear, and taking a long rest at the end of the day.

Making Ability Checks. On their turn, the character can make one ability check using any ability score and skill proficiency they like, as long as they can explain how this check could reasonably help them navigate the wilderness. For example, a character might make a Dexterity (Stealth) check, claiming that at the start of the day, they see a group of hobgoblins in a watchtower overlooking the wilds. Thus, the character’s Dexterity (Stealth) check could represent an attempt to sneak the party past the watchful hobgoblins. As long as the player can convince you that a given ability check could help the party, that check should be allowed.

The DC of this skill challenge is 15. If a character makes an ability check to progress the skill challenge and it doesn’t meet or exceed this number, their check is a failure. Otherwise, it is a success. On a failure, the character’s action results in the party being noticed by monsters. If this happens, you can either create a Hard to Deadly encounter using creatures of your choice, or roll once on the Grassland Encounters (Level 1–5) table in Xanathar’s Guide to Everything. Be careful, some of these encounters can be very hard for low-level characters, so make sure they know that they can try to run away! After an encounter, the characters continue traveling for the rest of the day, and then can take a long rest.

If the character succeeds on an ability check to progress the skill challenge, they find a safe place to rest for the night. This might be an abandoned fort hidden in a copse of trees, a camp of travelers heading north to Waterdeep, or even a group of friendly hobgoblins that defected from their unit and are willing to break bread with fellow travelers.

Success or Failure. The characters’ ultimate goal is to make it through the wilderness and leave the fell shadow of Dragonspear Castle. If the party accumulates a total number of failures equal to the number of characters in the party (not counting NPC followers) over the course of the skill challenge, they fail the challenge and become lost—ultimately wandering into the Trollclaws. Next week’s encounter will deal with the results of failure, though those encounters are also easily adapted to a successful party.

If the characters instead earn a number of successes equal to the number of characters in the party, they succeed! A successful party not only finds a relatively safe path through the Dragonspear Wilds, but also finds a tidy reward, as described in the “Conclusion” section, below.

Flavoring Random Encounters

When creating random encounters, you can heighten the atmosphere by choosing terrain or creatures that match where the characters are exploring. This also makes the players feel good, like their decision of where to explore had an effect on their journey. If they decided to cut straight through the ruins of Dragonspear, you could try using the map of Cragmaw Castle from Lost Mine of Phandelver and use humanoids like hobgoblins and bugbears as foes.

If they’re traveling across the fields outside of Dragonspear, you can use some of the grassy maps from Tactical Maps Reincarnated. You could even use associated encounters from Tactical Maps: Adventure Atlas instead of rolling for random encounters! On the other hand, if they travel through the hills and head for the Trollclaws, roll on the Hill Encounters (Level 1–4) table in Xanathar’s Guide to Everything, instead.


If the characters succeeded on this skill challenge, read or paraphrase the following:

The tall grass of the fields surrounding Dragonspear recede, and you think you can see a thin pillar of smoke in the distance, far off to the south-east. Hopefully, the worst of the wilderness is behind you. With a few more days’ travel, you’ll be at Boareskyr Bridge, and from there you’ll be back on the Trade Way in no time!

In addition to finding a safe way out of the wilderness, the characters also find a broken-down wagon. Inside is an oaken chest with a rusty and easily broken lock. The chest contains 2,000 gp worth of golden trade bars stamped with the crest of Baldur’s Gate. Finding an honest merchant who will buy this sort of easily tracked wealth will be hard, but someone with a criminal contact could find a fence the next time they’re in civilization.

If the characters failed this skill challenge, read or paraphrase the following:

You’re lost. It’s plain to see that wherever you were trying to go, you didn’t make it. You’re still just as deep in the wilderness as you were before, and the monster attacks aren’t showing any signs of letting up. Someone, or something, is surely tracking you through the tall grass. If you don’t make for cover, the attacks will probably only grow more and more frequent, until you’re overwhelmed.

There are hills to the south. Tall, craggy hills—known as the Trollclaws. They’re dangerous, but at least you’ll be able to see danger coming at you, instead of waiting blindly for them to ambush you in the tall grass. Will you travel to the hills?

If the characters don’t travel to the hills—the location of next week’s encounter—you can start this skill challenge over again; they lose all successes and failures, and can try again.

Finally, if the characters aren’t 3rd level by the end of this encounter already, they gain enough XP to advance to 3rd level, regardless of whether or not they succeeded or failed at this skill challenge.

Did you like this encounter? If you want to read more adventures, take a look at the other encounters in the Encounter of the Week series! If you're looking for full adventures instead of short encounters, you can pick up the adventures I've written on the DMs Guild, such as The Temple of Shattered Minds, a suspenseful eldritch mystery with a mind flayer villain (for 3rd level characters). My most recent adventures are included in the Platinum Bestseller Tactical Maps: Adventure Atlas, a collection of 88 unique encounters created by the Guild Adepts, which can be paired with the beautiful tactical poster maps in Tactical Maps Reincarnated, recently published by Wizards of the Coast.

James Haeck is the lead writer for D&D Beyond, the co-author of  Waterdeep: Dragon Heist and the Critical Role Tal'Dorei Campaign Setting, the DM of  Worlds Apartand a freelance writer for Wizards of the Coast, the D&D Adventurers League, and Kobold Press. He lives in Seattle, Washington with his partner Hannah and their feline adventurers Mei and Marzipan. You can usually find him wasting time on Twitter at @jamesjhaeck.


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