Princess in a Tower

A family-friendly adventure for 1 to 4 characters of 1st to 5th levels.


This adventure was designed for a single character of 1st to 5th level. It’s recommended that the combined character levels equal at least 5. This adventure relies on role play, exploration, problem-solving, and a skill challenge. There is the opportunity for combat at several stages of the adventure.

This adventure was inspired by a Nerdarchy video and Patrick Rothfuss who both showed me how fun and easy it is to turn a classic fairy tale on its head.

Adventure Hook(s)

Many a brave adventurer has set off into those woods in search of the witches’ tower where the princess and heir to the throw of our neighboring kingdom has been imprisoned since she was a young girl. It’s said that the tower is guarded by an evil dragon.

One young adventurer survived to tell the story of his encounter with the dragon so huge, it slept curled around the entire tower. He described the collapsed ruins with one tall tower still standing. The dragon guards more than just the beautiful princess. It guards a huge treasure made up of all the armor, swords, and money carried by all the adventures that have ever try rescuing the fair maiden.

The young man drew a map to a ruined castle in the middle of the dense forest and sold it to the innkeeper. For a small price, the innkeeper will sell you a copy.

Many of the locals at the inn will gladly tell you about the neighboring kingdom and the reward for anyone that can return the princess home. The reward is said to be your weight in gold for her safe return. If you can return with proof you killed the dragon, you get twice your weight in gold! 

Player Goals

  • Explore the wilderness to find the dragon’s lair.
  • Kill the evil dragon.
  • Rescue the princess and return her home.
  • Teaming up with an NPC will greatly increase the chances of success.

Complications & Opportunities

There are several ways you can turn this story on its head. Each alternate version of the story provides different complications and opportunities.

  • The dragon is the captive and the “beautiful princess” is really an evil witch that set this whole thing up to lure adventures into her lair. The witch starves the dragon, forcing it to eat the adventures and their horses.
  • The dragon is a prince that was transformed by the king’s wizard. The princess flew away with the dragon so they could be together. They would trade all that they have to anyone that could break their curse.
  • The dragon is the princess and she is magically chained to the tower. The cruel witch uses magic to steal the pricesses’ beauty and youth.
For our version of the adventure, we are going with… The dragon is the princess. She doesn’t want to fight or hurt the adventurers, but the witch cast a spell on her, forcing her to defend the tower and everything in it. 
  • If the player can get the witch out of the castle the dragon would attack her.
  • If the player can find a way into the castle, the dragon won’t allow them to leave with anything they found inside.
  • There is a substantial treasure hoard, but it will be difficult to transport from this remote location. The witch is a hoarder, so the characters will have to spend a long time searching through all the useless stuff to find anything of value.

Breaking the spell:

  • If the witch dies, the spell is broken.
  • Breaking the amulet the witch wears around her neck will break the spell.
  • Destroying the tower will break the spell.
  • The dragon can’t willingly leave, but if the player can get the dragon at least 1 mile from the tower, the spell will break.
  • Casting Remove Curse or a Wish will break the spell.

Wilderness Survival/Exploration

With map in hand, the adventurer need only negotiate the wilderness and the dangers that hide within. See the Random Encounters below.

I also recommend a couple of skill challenge obstacles along the way. Here are a couple of options. These are fail-forward obstacles. They won’t stop the adventure, just slow it down and cause the loss of some equipment and maybe some hit points.

  • RIVER CROSSING – Thunder echos through the sky. Rain clouds hover over the mountain tops several days ride from here. When you arrive at the stream marked on the map, it is a fast-flowing river. The map shows this is the safest place to cross.
    • 3 successful dexterity checks are required to cross the river. (See DC and Skill Check on the Words! post)
    • 1st Failure – You slip on the slick, moss-covered stones. It is difficult, but you manage to regain your footing.
    • 2nd Failure – You step forward and the stones slip out from under your feet. Instead of solid ground, you plunge into a hole. The water carries away some of your gear while you struggle to keep your head above water. Finally, you find the other edge of the hole.
    • 3rd Failure – Focusing on your footing, you miss seeing the small tree being carried downstream.  The water in this section of the river is waist deep and the tree hits you in the chest, knocking the wind out of you. You cling to the tree as it spins and turns, flowing down the river.
    • 4th Failure – The water carries you very far down the river before finally getting stuck against the shore. Shivering and cold, you look up the river bank and see bits and pieces of your belongings. After a few hours of careful searching, you manage to collect most of your gear and make camp. 
  • IT’S A CLIFF – Well that is what this squiggle on the map is, a cliff. the shear wall of the cliff rises up about 30 feet here. Examining the map you see the squiggle intersects with. the river a few miles in both directions. Squinting at the map you see an x marked on the line. A short hike down the cliff line, you find a very narrow path that looks like it could be a way up. Looking closely, you see there are pitons (climbing spikes), but no ropes.
    • 3 successful athletic or acrobatic or athletics checks will get the character up the narrow path.
    • 1 Failure – slick from the rain, your foot slips. You scrabble for a grip and manage to grab a root.
    • 2nd Failure – Trusting your weight to one of the pitons, you pull yourself up a little further. Before you can get a firm footing, the piton comes loose. You slide several feet before stopping. Scrapped and bruised, you start your climb again.
    • 3rd Failure – The stone you are holding onto loosens and falls away. More loose rocks fall from above. Several large stones bounce off your backpack. You barely manage. to keep your grip until the last of the sand and small rocks stop raining down.
    • 4th Failure – Finally, the top of the cliff is within reach. You see a rope hanging over the lip, just inches over your head. You gently pull, it seems secure. You give it a little harder tug and a backpack full of supplies falls over the cliff. For a moment you think you can hold onto the rope and save the supplies. You watch it fall in slow motion over your head and as it falls past you, you get a good look at the ground below. Reflex takes over and you let the rope go and reach for a solid grip on the cliff wall.

D&D Wilderness Maps

The Tower

Tower Map by Dyson Logos

Tower may by Dyson Logos. (

The Dragon: Brass Dragon Wyrmling

DANGER!!! A dragon can kill a fourth-level character with one attack. Direct combat with a dragon is a really bad idea for the player. Encourage them to find alternative ways to solve this part of the adventure.

If they choose to fight anyway, the dragon will use its Frightful Presence to scare the adventurer away instead of attacking. You can also scale the damage output for the character level. If the character runs out of hitpoints, see my article on Removing Death from Dungeons & Dragons

Being forced to fight, the dragon will announce her attacks before using them. For example, “Let’s see if you can dodge my breath weapon!” Having foreknowledge of the coming attack gives the adventurer advantage (roll 2d20 and take the highest) on their roll to dodge.

The stats below are provided for games with older kids and parties of more than one character. For younger players or players at low levels, I recommend the # of hits method for combat. Basically, figure out how many “solid” hits are needed before the dragon “goes down.” You can still have the player roll dice for damage, but you really don’t need to keep track of hitpoints.

Str 15 (+2) 50%
Dex 10 (+0) 33%
Con 13 (+1) 43%
Int 10 (+0) 33%
Cha 13 (+3) 43%
Int 10 (+0) 33%
  • Saving Throws Dex +2, Con +3, Wis +2, Cha +3
  • Skills Perception +4, Stealth +2
  • Damage Immunities Fire
  • Senses Blindsight 10 Ft., Darkvision 60 Ft., passive Perception 14
  • Languages Common, Draconic
  • Challenge 1 (200 XP)
  • Legendary Resistance (3/Day). If the dragon fails a saving throw, it can choose to succeed instead.


  • Special Attack: The dragon can use its Frightful Presence.
  • Bite. Melee Weapon Attack: +4 to hit, reach 5 ft., one target. Hit: 7 (1d10 + 2) piercing damage.
  • Frightful Presence. Each creature of the dragon’s choice that is within 120 feet of the dragon and aware of it must succeed on a DC 16 Wisdom saving throw or become frightened for 1 minute. A creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success. If a creature’s saving throw is successful or the effect ends for it, the creature is immune to the dragon’s Frightful Presence for the next 24 hours.
  • Breath Weapons (Recharge 5-6). The dragon uses one of the following breath weapons.
    Sleep Breath. The dragon exhales sleep gas in a 15-foot cone. Each creature in that area must succeed on a DC 11 Constitution saving throw or fall unconscious for 1 minute. This effect ends for a creature if the creature takes damage or someone uses an action to wake it.

The Witch (Wizard)

Rosaline Farrow, Female Human, 5th Level Wizard 

DANGER! Rosaline is a glass cannon. She can easily kill a single fourth-level character, but can’t take much damage. 

The witch uses Misty Step to come and go from the castle because the dragon will attack her if she’s given the chance. The player character will see her do this when they first arrive. This gives the PC time to observe her and maybe set a trap/ambush for her.

Medium (4’10”) Human, Neutral Evil
Armor Class 8
Hit Points 13 (5d4)
Speed 30 ft.

15 (+2) 7 (-2) 10 (+0) 15 (+2) 13 (+1) 12 (+1)

Skills Nature +5
Senses Passive Perception 11
Languages Common, Giant, Terran
Attacks Melee +5 / 2d4+2, Ranged +1 / 2d4-2, Grapple +2

  Spell Save DC  0 1st 2nd 3rd
Spell /Day 13 4 3 2 1

Spells: Firebolt, Mage Hand, Ray of Frost, Shocking Grasp, Burning Hands, Disguise Self, Sleep, Hold Person, Misty Step, Fireball

Battle Strategy: Rosaline would prefer to not do battle if possible. If she detects the PC coming, she will attempt to cast Sleep on him/her. If the Sleep spell doesn’t work, she will use Disguise Self to make herself look like a beautiful princess then use Hold Person at the first opportunity. If forced into close combat, she will use Burning Hands or Shocking Grasp. Her goal will be to use Misty Step to put distance between her and the PC then use Fireball to finish the PC off.

Description: Rosaline wears what was once a very beautiful dress fit for a princess, but it has long since suffered many rips, tears, stains, and smells of body odor. She is muscular with a powerful set of arms. She keeps her long auburn hair kept up in a ponytail. She is surprisingly sunburned and her eyes are piercing gray.

Personality: Confrontational and loud best describe her. She is terrible with names. She forgets people’s names several times before they finally stick; this causes her no end of embarrassment.

History: Born to a poor family in the city she treasured whatever gifts she got. When money was particularly tight she took to the alleyways. She found that a few simple magic spells could get her almost anything she wanted except beauty and love.

Motivation: She wants random interesting trinkets and junk, hates to throw anything away; and a wizard she once robbed is out to get her. She is hiding here in the tower planning her next big move.

Flaws: Crazy, spiteful, forgetful, and greedy.

Bonds: She will do anything to protect her pet, Flopsie. She is convinced that her shawl is actually her cat and that her cat is actually her husband who was turned onto a cat by the wizard she robbed.

Voice: Tuts and clicks tongue

Appendix: NPCs

Appendix: Random Encounters

The following encounter table is to be used for the road, woods, and grounds of the castle. Most wild animals will flee combat when injured unless they see the player as a potential meal.

2D10QtyNameAward XP EachTotal Award XP
1-5No encounter: You heard something, but couldn’t find the source of the sounds.
61Giant Poisonous Snake50250
91d4+1Giant Centipede50450
131d10Elven warriors50150
141Swarm of Rats5050
15-191d4Giant Rats2550

All creatures are also taken from the basic rules and/or Monster Manual.

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