50 Overnight Encounters

Any band of adventurers worth their salt will take their time to set up a watch for the night. More often than not the night passes uneventfully and the journey slogs along. Sometimes you want something to shake your group up a bit, without resorting to a wandering monster.

All of these could range from unexplained occurrences to hooks for you to base entire adventures off of. It just depends on what you need for your game at the moment. I find that occasionally tossing in something like this will help to keep everyone engaged during long periods of travel.

These also work as good fillers, when I need something else to happen prior to the end of a session. Whatever the case, roll a d100 and consult below, to see what goes bump in the night.

1-2. Celestial Spectacle: The night sky comes alive with a breathtaking display of shooting stars or a rare planetary alignment.

3-4. Harmonious Melody: Enchanting music fills the air, seemingly emanating from an unseen source. The music is not loud enough to wake anyone up and will cease if any sleeping party members are awakened.

5-6. Glowing Fauna: Bioluminescent creatures emerge from the darkness, illuminating the surroundings with their ethereal glow.

7-8. Astral Projection: One of the sleeping characters experiences a vivid and prophetic dream, offering hints or warnings about their future endeavors.

9-10. Whispers in the Dark: Those on watch hear faint whispers or distant voices, carried on the night breeze. These hint at hidden secrets or long-lost knowledge.

11-12. Ghostly Encounter: A friendly or troubled spirit manifests during the night, seeking closure or offering guidance to the characters.

13-14. Lost Artifact: The characters on watch stumble upon a forgotten relic or artifact, partially buried in the ground, with unknown powers or a mysterious past.

15-16. Dream Realm: Sleeping characters find themselves in a shared dream, navigating a surreal landscape or confronting their deepest fears.

17-18. The Illuminated Path: Characters on watch notice a faint, glowing trail leading to a hidden location or an important discovery.

Standing watch. Art by: © 2015 Dean Spencer, used with permission. All rights reserved.

19-20. Time Warp: Sleeping characters experience a temporary time distortion, witnessing events from the past or glimpses into the future.

21-22. Shifting Shadows: The campsite becomes a gateway to a pocket dimension or a parallel reality, where familiar places are twisted and distorted.

23-24. Animal Messenger: An intelligent animal approaches the camp, bearing a message or a warning from a distant ally or foe.

25-26. Flickering Flames: The campfire dances and morphs into mesmerizing shapes, revealing cryptic symbols or visions to those who observe it.

27-28. Enchanted Sleep: Characters on watch drift off to sleep. When the party wakes, they find themselves in a different location, seemingly transported during their slumber.

29-30. Nature’s Blessing: A light rain starts out of nowhere. As it lets up, the characters wake up to find their wounds healed, their supplies replenished, and a sense of rejuvenation.

31-32. Moonlit Ritual: A secretive group performs a ritual under the moonlight, offering the characters on watch a chance to witness or interrupt their proceedings.

33-34. Nighttime Market: A mysterious bazaar materializes near the campsite, offering exotic goods, rare ingredients, or peculiar services.

35-36. The Invisible Hand: The characters wake up to find objects around the campsite rearranged or tidied up by an unseen helpful presence.

37-38. Luminescent Guardian: A gentle spirit of light takes on the role of protecting the characters during the night, guiding them away from harm.

39-40. The Shadow’s Beckoning: Shadows in the surrounding area come to life, swirling and forming shapes, hinting at hidden paths or secrets.

41-42. Portentous Clouds: Strange cloud formations gather above the campsite, revealing foreboding symbols or images that foreshadow future events.

43-44. The Whisperer: A mysterious figure emerges from the darkness, claiming to possess ancient knowledge and offering cryptic advice.

45-46. Trapped in a Dream: One of the characters becomes trapped in a vivid, lifelike dream, requiring the others to find a way to wake them.

47-48. Phantasmal Menagerie: A collection of spectral animals gathers around the campsite, observing the characters with curious, ethereal eyes.

49-50. Nighttime Companion: A loyal and intelligent creature approaches the characters, seeking companionship or offering assistance during their travels.

51-52. Veil of Illusion: The characters wake up to find themselves in an illusionary realm, where reality bends and shifts, requiring them to solve puzzles to escape.

53-54. Elemental Reverie: The elements around the campsite come to life, dancing and swirling in a mesmerizing display of elemental harmony.

55-56. Echoes of the Past: The characters witness ghostly echoes of historical events or significant moments that occurred in the area, gaining insights into its hidden history.

A cozy campfire as the party prepares to turn in for the night. Art by:© 2015 Dean Spencer, used with permission. All rights reserved.

57-58. Feywild Crossing: The campsite becomes a temporary gateway to the Feywild, where the characters encounter mischievous fey creatures and experience the whimsical nature of the plane.

59-60. Shadow Puppetry: Shadows cast by the campfire take on a life of their own, performing a silent and captivating shadow play that tells a mysterious story.

61-62. Whispering Trees: The trees surrounding the campsite whisper ancient secrets or foretell future events to those who listen closely, providing valuable information or warnings.

63-64. Elemental Balance: The characters are visited by an elemental spirit that offers them a unique and temporary boon related to one of the four elements—earth, air, fire, or water.

65-66. Vanishing Act: The campsite suddenly disappears, leaving the characters in an otherworldly realm or plane for a short time before reappearing in a different location.

67-68. Illusory Menace: Characters on watch are plagued by illusory creatures or illusions that mimic dangerous foes, testing their wits and abilities.

69-70. Spirit Guide: The characters encounter a wise spirit guide who provides guidance and cryptic advice, leading them to hidden treasures or revealing important information.

71-72. Ephemeral Guardians: Ethereal and translucent guardians appear around the campsite, protecting the characters from harm during the night.

73-74. Haunted Dreams: Sleeping characters share a collective dream haunted by the spirits of the past, requiring them to confront and resolve a forgotten tragedy.

75-76. Luminous Dew: The morning reveals that the campsite is covered in sparkling and magical dew, which can be collected and used for various enchanting purposes.

77-78. Aurora’s Embrace: The sky fills with vibrant auroras, and the characters are enveloped in their mesmerizing glow, temporarily granting them supernatural abilities or insights.

79-80. Time Loop: Characters on watch drift off to sleep. Then the night repeats itself, with the characters reliving the same events and encounters until they discover the cause and find a way to break the loop.

81-82. Feywild Market: A bustling Feywild market manifests near the campsite, offering strange and exotic goods, curious trinkets, and intriguing bargains.

83-84. Cursed Relic: Characters on watch stumble upon a cursed object that brings misfortune or strange effects until they find a way to cleanse or dispose of it.

85-86. Lunar Serenade: The moon’s radiant light fills the campsite, soothing and invigorating the characters, granting them temporary bonuses to their abilities.

Adventurer catching a few winks. Art by Diego Castro. Used with permission. All rights reserved.

87-88. Guiding Stars: A constellation forms in the night sky, providing guidance and navigation aid to the characters, helping them find their way or revealing hidden paths.

89-90. Feywild Poltergeist: A playful and mischievous fey creature infiltrates the campsite, pulling harmless pranks and challenges the characters to a game or contest.

91-92. Arcane Nexus: Characters on watch discover a site of potent magical energy, where spells behave unexpectedly, wild magic surges, and magical phenomena occur.

93-94. Shadow Gate: Characters on watch discover a hidden portal to a plane of darkness and gloom, where they must navigate treacherous shadows and confront shadow creatures.

95-96. Ethereal Visitors: Ethereal beings or spirits from another plane temporarily materialize at the campsite, seeking assistance, guidance, or redemption.

97-98. Starfall: A shower of shooting stars rains down upon the campsite, each carrying a mysterious and magical effect when collected or interacted with.

99-100. Night’s Blessing: The night bestows a temporary boon upon the characters, enhancing their abilities, granting them insight, or imbuing them with a sense of profound luck and fortune.

That is all for now. I hope these additions bring a bit of wonder to your party’s overnight experiences. Thanks for stopping by. If you have any suggestions for other encounters, please leave a note in the comments.

If you would like to see my other random lists, you may find them here. My maps with plot hooks are collected here. Have a great week!

The Hall of Tentacles

This week I am focusing on an individual encounter. Our basic D&D group was nearing the end of their second arc of adventures, and I put The Hall of Tentacles together to give them a challenging boss fight.

My villain was initially a lone spellcaster. This presented me with a challenge in terms of how to set up the fight and make it entertaining for my players. I wanted to avoid an anti-climactic fight, where the 5 party members simply rushed the antagonist and beat her into submission. On the other hand, if I built her strong enough to take a beating, my fear was that she would be too deadly.

I settled on using a bit of DM fiat and making up some special mechanics & creatures specifically for this fight. While my players are fairly new to the hobby, I wanted to keep them on their toes. Rather than pulling directly from the Rules Cyclopedia or Creature Catalog, I created some things of my own. If you are a stickler for RAW, this type of thing might not be for you. That said, my group was really engaged for the duration of the fight and at times you could cut the tension with a knife.

As always, I will keep this system agnostic and refrain from any specific stats. Instead, I’ll simply lay out what worked from me. Hopefully it will be useful to spark some ideas for your own games. From there it should be an easy matter of dialing things up or down to suit your needs.

The Setup

A Kosantian witch named D’Sara Shahari has been the driving force behind a number of the party’s early adventures. Hoping to impress her patron, she has been on a streak of dastardly deeds. D’Sara has recently taken up residence in Rohrbach Castle, on the outskirts of the small village of Brindle.

Baron August Rohrbach has always dabbled in the dark arts. Never able to obtain any real power, he leapt at the chance to offer shelter to the witch and hopefully learn her ways. Unfortunately for the nobleman, he learned too late that D’Sara had no desire to take on a pupil but rather was interested in something sinister below the castle.

Over the past few weeks, the witch has effectively taken control of Rohrbach Castle. Most of the staff have run off and the baron has been reduced to being her mindless thrall. Gaining access to the laboratory in the catacombs under the keep, she summoned a tentacled horror from the murky waters below. Having kidnapped two young children from the nearby village, she plans to sacrifice the youths in a gesture to honor her patron.

The party tracked D’Sara to Brindle, where they learned of the missing children and gathered enough intel to believe that the witch was residing within the castle walls. After surveilling the structure, the party discovered a cave entrance along the riverbank.

Wading through ankle-deep water and catching occasional glances of something slithering on the periphery, the party made their way through the caverns below the castle. Finally coming to higher ground, they saw light coming from the passageway to the north. This ultimately lead them to location #13, the entrance to the laboratory cavern.

The wicked D’Sara Shahari. Artwork © 2015 Dean Spencer, used with permission. All rights reserved.

The Laboratory Cavern

This large room is well lit with torches around its circumference. Tables with various jars, bottles, and equipment will make it immediately clear to the party that this is some type of laboratory.

Already aware of the party’s presence, D’Sara will be waiting for them at the top of the stairs (location #14). Baron Rohrbach stands nearby (location #15) awaiting the bidding of his master.

Interspersed about the room are 12 pools, open to the water below. Each is circled with a bronze band featuring strange runes. The reflection of the torchlight on the water gives the cavern’s ceiling a queer look, as if it is undulating.

Suspended 10’ over the pool at location #3 is an iron cage holding Ulli & Greta Stoll (the children from the village). The cage is held by a rope that goes up to the ceiling and then over to the far wall (location #16) where it is tied off.

The Fight

When the party enters the room, allow them a moment to take in their surroundings. Unless immediately rushed, D’Sara will deliver a villainous soliloquy and the children will call out for help. As soon as any of the party members start to close the distance to either the children or D’Sara, roll for initiative and the encounter will begin in earnest.

The crone has no intention of going toe to toe with a party of adventurers. She will hold her position and hurl spells at the do-gooders when they come within range. If things start to go poorly for her she will not be averse to the concept of turning and attempting to flee.

Baron August Rohrbach. Art by Bartek Blaszczec.

Baron August Rohrbach has been under the witch’s spell for weeks and is barely clinging to his humanity. Gaunt from lack of food, he could easily be mistaken for some type of undead. At this point he is really no more than an automaton mindlessly following orders. Dressed in his family’s ceremonial plate armor and carrying a longsword, the baron moves at 50% of the speed of a normal human.

His ensorcelled state will leave him immune to charm or fear effects. He should have fairly high HP but only dish out moderate damage. He will ignore ranged attacks but will immediately turn and engage anyone who enters into melee with him

With a word from his mistress at the start of the fight, Baron Rohrbach will shamble to location #16 and start hacking at the rope that holds the children’s cage over the pool. Unless interrupted by the party, he will succeed in cutting the rope in 3 rounds and the cage will splash into the pool below.

If the rope is cut and the cage hits the water, it will be fully submerged within 2 rounds. The combination of cage and children weigh a total of 190 lbs. The water under the cavern is shallow enough that the cage may be reached even if fully under water. The children will perish if they are underwater for more than 3 rounds.

If the evil witch, her mesmerized lackey, and the trapped children were not enough, the party will face one final peril. D’Sara chose this location because she wanted to make a sacrifice honoring her patron. She knew of an unspeakable horror residing in the river that runs alongside the castle. This tentacled monstrosity is lurking and waiting for an opportunity to strike.

Grid/No labels

I never had any intention of having my group face some giant beastie here. However this served to build the tension while also making the encounter more interesting. At the top of every round, roll a d12. A hideous pink tentacle will then burst out or the corresponding pool. The tentacles have a reach of 5’ from their point of origin and will attack the closest party member that they can reach.

Play with the tentacle mechanics as you see fit, based on the level and capabilities of your party. For my group, I kept things easy and avoided bogging things down. I had a hit indicate that a tentacle had grabbed the party member. A grabbed party member would suffer 1d4 points of damage from being constricted each round that they were grabbed. They could not move and made attacks with a -1 penalty. Grabbed party members are freed either through destroying the tenacle (I made this relatively easy, giving each tentacle only 4 HP) or after making a successful “Open Doors” check.

The tentacled creature itself will never make a full appearance. Once D’Sara has been dealt with or fled, the tenacles will retreat into the murky depths.


This yielded a fun encounter for our group. I realize it is a bit unorthodox, but it gives you a number of variables to tune as needed in order to challenge your party. The abilities for D’Sara & Baron Rohrbach are obviously wide open for you to play with. The tentacles themselves could easily be tweaked by adding greater frequency, longer reach, or more damage.

No grid/No labels

I purposely strayed from known creatures and tried to focus on mechanics that would make for an exciting evening around the table. Thinking back to Robert E. Howard or HP Lovecraft stories, I always enjoyed how the abilities and origins of magic users or eldritch horrors were left very vague. While it may be blasphemy to some, I think it avoids a lot of meta gaming on the player side to keep them on their toes a bit and show them something that they have not seen before.

Thank you for stopping by. Please take a minute to say hello and if you’d like to read some more, here are some convenient links

All of my posts detailing the locations in Cross Tree are located here.

For a list of all of my adventure hooks with maps, click here.

My random tables are collected here.

Finally, I’ve stuck everything else here.

Good Gaming!