WATERDEEP MYSTERIES

VINCENT TRENCH
PRIVATE EYE

TITLE RIGHT SIDE 1

 WATERDEEP MYSTERIES
CREDITS
Crafted by Paul Metzger @metzpaul and
Kathleen Harrington @KatnBR
Cover art © 2020 Stéphane "Wootha" Richard.
Full page feature artwork by Newell Wyeth.
Additional artwork by Edwin Abbey, Charles
Bennett, Charles Keene, Phil May, and Albert
Robida.
Some artwork courtesy Wizards of the Coast
Dungeon Masters Guild Creator Resources.
Page background and watercolor splashes
designed by lifeforstock / Freepik.
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This work contains material that is copyright
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Community Content Agreement for Dungeon
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All other original material in this work is
copyright 2022 by Paul Metzger and published
under the Community Content Agreement for
Dungeon Masters Guild.
First edition. April 2022.
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OVERVIEW
Waterdeep, City of Splendors Mysteries! This
supplement is designed to aid Dungeon Masters
in creating and running mystery-themed
adventures in the course of Waterdeep: Dragon
Heist or any other campaign set in the Crown of
the North.
We begin in Trollskull Alley, where Dragon
Heist adventurers set up shop near the Tiger’s Eye
detective agency. You’ll learn the story of its
proprietors, Vincent and Katie Trench.
Why merely grant your adventures
investigative results for 50 gold when you can
lead them through the investigation on their own?
Young Katie Trench is presented as an
investigative sidekick to assist, gaining new
abilities alongside the adventures as they progress
through level 10.
Next is a framework for creating your own
mystery adventures, with advice drawn from
proli c authors in the pulp detective genre.
Fifteen mysterious locations follow, spanning
all the wards of Waterdeep. Providing avorful
settings for scenes in your adventure, they feature
interesting NPCs and ideas for plot hooks.
Rounding things out are three new magic items
utilized by the Trench family. Give them to your
villains to assist their dastardly schemes and as
rewards for your investigative player characters.
Mystery awaits you in Waterdeep!

VINCENT TRENCH
Vincent Trench doesn’t like to think about
Valantajar.
It’s hard for Vincent Trench not to think about
Valantajar when he wears the fur every night.
Katie insists. Vincent Trench loves his daughter
with all his heart. He’d do anything for her.
Wearing the fur makes her happy, so he wears the
fur. He got her some of her own. She never takes
it off. Wearing the fur makes Katie happy, so it
makes Vincent Trench happy. But it reminds him
of Valantajar.
Vincent Trench loves his daughter with all his
heart. He’d do anything for her. He’d kill for her.
He’s done it before. Vincent Trench doesn’t like to
think about who Vincent Trench was before
Valantajar killed him. Vincent Trench was not a
good man. Vincent Trench took people’s children.
Valantjar took Vincent Trench’s child. Seemed fair.
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Valantajar
Valantajar was on a simple mission for a Duke of
Hell: in the guise of a human, in ltrate a certain
major city on the Material Plane and gather
information for a planned invasion and take-over.
He was to keep a low pro le, send regular
reports, speak to no other Duke, and remain in
the city until ordered to leave. Then the Duke was
destroyed on her own plane and Valantajar, still
bound by his orders, was stranded. That was 250
years ago, and in the interim, Valantajar has come
to rather enjoy his exile.
With excellent libraries, wonderful teas, ne
wines and cognacs, catnip, seafood, and no one
giving orders, only one thing was missing—
sating his appetite for humanoid esh.
Disappearing the city’s populace didn’t exactly
t in with keeping a low pro le. Additionally,
Valantajar found the mortals much more
interesting than he rst anticipated, coming to
respect and even admire them as they spent their
short lives trying to make sense of their world. He
found their children to be particular delights. He
also found that some humanoids were capable of
completely rede ning his concept of evil.
In that, Valantajar found his purpose. He
hopped between identities, seeking out those
preying on children and teaching them what it's
like to be the prey.
One day a particular prey had a child of his
own: his 2-year-old daughter he absconded with
after murdering the little girl’s mother. Valantajar
knew he had found a new duty.
The Tiger’s Eye
In addition to the toddler, Vincent Trench came
with paperwork. A lot of it. It gave Valantajar
everything he needed. Wealth. Underworld
contacts. Legitimacy. All the resources to learn the
terrible things Katie Trench’s father had done—
and tie up all the loose ends.
So Valantajar settled down. He commissioned a
magic ring to let him be Vincent Trench, not
merely appear as him. He took on as an honest
profession the type of work he had engaged as a
hobby. The name of his agency seemed clever at
rst, but now it reminds Vincent Trench of
Valantajar. Sometimes it’s good to remember.
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 KATIE TRENCH
Katie will keep humoring her father. He’s the
best father in all the Realms, and there isn’t
Katie Trench knows that Vincent Trench isn’t her anything Katie wouldn’t do to make him proud.
father. Or rather, her father isn’t really Vincent She’s going to keep studying hard and one day
Trench. Katie Trench isn’t a fool. get to be a good enough investigator to run the
family business.
Katie is an investigator. She’s known for years.
I mean, c’mon, it’s not that hard to gure out. For
one thing, her father has looked the same, like,
Junior Investigator
forever. Sure, she doesn’t remember when she Katie’s father paid a great deal of attention to her
was really little. She doesn’t remember coming to education. In addition the reading, writing,
Waterdeep, but she does remember most gures, and professional skills he was able to
everything after. Her father has looked exactly the impart himself, Vincent Trench also employed
same as long as she can remember. He even has two neighborhood friends, Fala and Rishaal, as
the same stubble every single day, but she’s never supplemental tutors.
once seen him shave. After her constant protestations that she was, in
The fact that he hangs out as an awesome cat fact, “old enough,” her father allowed Katie to
monster every night is also pretty big piece of start her apprenticeship earlier than he would
evidence. have preferred. She’s proven herself to be quite
capable, and recently Vincent granted Katie near-
Yeah, he puts on a headband “just like hers.”
total autonomy to pursue the cases he assigns to
But his timing isn’t always perfect. And cat
her as she sees t—although he requires her to
monster dad feels different than human dad does.
remain attuned to a guardian’s bracelet with him,
Besides, she’s checked out the headband. Magic it
which limits her movements to within the city
ain’t. Plus hers doesn’t make her hands
walls and excludes her from the Field Ward. Katie
backwards. That’s how she came to realize that
says it’s a small price to pay to be allowed free
her father is a raksasha. An immortal tiger god
roam of the city. Although she won’t openly
from the Nine Hells. How hurling cool is that!
admit it, she feels secure in the knowledge that
Katie Trench isn’t sure if her father knows that her father will appear and claw to bits any bad
she knows. He must know, right? Vincent Trench guys who happen to get the better of her.
isn’t a fool.
But he still plays cat with her every night.
That’s being a good daddy. If your daughter is still
eight years old! She’s ten now! He is being just
ridiculous. Or maybe he’s more comfortable in his
own fur. Katie wouldn’t want to take that from
him.
Sure, Katie still wears the headband that
costumes her as a cat person during every waking
moment. Who wouldn’t? It’s awesome! Maybe
when she was little it was playing cat. But she’s a
mature pre-tween now. It’s a fashion statement.
When she gets married—a young, beautiful, rich
tabaxi is going to sweep her off her feet—all of
her bridesmaids are going to wear fur.

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 KATIE TRENCH SECOND LEVEL
Hit Points 13
Investigator Sidekick
Small Humanoid (Human), Chaotic Good Streetwise
Armor Class 12 Having thoroughly explored the city, Katie
Speed 30 ft. possesses a nearly perfect mental map of
Waterdeep with the exception of the Field Ward.
Strength 8 (-2) She can accurately estimate the travel time, and
Dexterity 16 (+3) provide the best route, to any named street or
Constitution 10 (+0) alleyway in the city.
Intelligence 15 (+2)
Wisdom 12 (+1) Katie also recalls the location of a speci c
Charisma 13 (+1) business, public building, or noble villa on a
successful DC 15 Intelligence (History) check. On
Saving Throws Dexterity, Intelligence a failure, she is unsure of the exact location but
Skills Acrobatics, Investigation, Persuasion,
chooses a location in a random direction a
Sleight of Hand, Stealth
Senses passive Perception number of streets away equal to the amount she
Languages Common, Dwarvish, Elvish, failed the check by.
Infernal
THIRD LEVEL
FIRST LEVEL Hit Points 18
Hit Points 9
Budding Musician
Proficiency Bonus Katie gains pro ciency with the lute. Her
Proficiency Bonus +2 instructor, Lillian Than, is a graduate of the
College of New Olamn and a member of the
Well Educated Harpers. Katie’s reputation as an investigator has
Her father having seen to her schooling, Katie is earned her a bit of renown with the organization.
learned in a number of areas. Katie can acquire common and uncommon
potions and scrolls (but not any that can cause
Investigative. Katie’s pro ciency bonus is
physical harm) at 75 percent of the usual price
doubled for Intelligence (Investigation) checks.
from Lady Than, and the Harpers are usually
Magical Scholarship. Katie’s spellcasting willing to share any information they posses
ability is Intelligence. Spell save DC = 8 + her related to Katie’s investigations.
pro ency bonus + her Intelligence modi er (12 at
1st level). She uses her family signet ring as a
spellcasting focus.
Katie knows the druidcraft and mage hand
cantrips, which she can cast at will. She can also
cast silent image. After she does so, she cannot cast
it again until she nishes a short or long rest.
Well-Spoken. Katie is pro cient in the
Persuasion skill. She speaks Dwarvish, Elvish,
and Infernal in addition to Common. When a
creature Katie can hear speaks in thieves’ cant
there’s a 50 percent chance she notices. When she
does so, Katie can decipher the hidden message
with a successful DC 15 Intelligence
(Investigation) check.

Lady Lillian Than

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 FOURTH LEVEL
Hit Points 22

Ability Score Improvement

Intelligence 16 (+3)
Charisma 14 (+2)

Friends in Low Places

Katie is a friend to the street urchins of
Waterdeep, openly sharing food and other small
comforts, and joining in their games and mischief.
For an example of some of her friends, see the
sidebar “The Three Urchins” in chapter 4 of
Waterdeep: Dragon Heist.
The children pass on small titbits of
information, which gives Katie a +5 bonus to
Intelligence (Investigation) checks made on the
streets of Waterdeep.
Katie also knows who the youth leaders of the
street gangs in each of the city’s wards are. In
mutual agreement with her father, that’s as close
as Katie ever gets to the world of organized crime. Gambling street urchins
When Katie is seeking information from the
Xanathar’s Guild or the Zhentarim, she’s always
sure to add some hopefully useful information
when she asks one of her shady youth FIFTH LEVEL
acquaintances to run something up the chain of
Hit Points 27
command.
The DM should make the determination on Proficiency Bonus
how the third party interaction plays out based on Proficiency Bonus +3
the facts behind the scenario, possibly by
consulting the following table: Insightful Interviewer
d6 Outcome Katie gains pro ciency in the Insight skill, and
doubles her pro ciency bonus for Wisdom
1 Katie’s request doesn’t reach anyone of significance
(Insight) checks she makes when attempting to
in the organization.
determine if a creature is deceiving her.
2–4 Significant figures inside the organization become
Katie also learns detect thoughts. Once she casts
aware of Katie’s request, but no response is offered.
it, she cannot cast it again until after she
5 Information from inside the organization crafted in completes a long rest.
such a way as to advance its own agenda comes
back to Katie.

6 Useful and true information from inside the

organization comes back to Katie.

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 SIXTH LEVEL
Hit Points 31
Confidential Source
Through her work with her father for the Tiger’s
Eye, Katie has gained the con dence of Gaxly
Rudderbust, publisher of the Waterdeep Wazoo.
The Wazoo specializes in publishing the affairs of
the Waterdhavian nobility, and Rudderbust is
very careful to only print what is veri ably true.
But Between You and Me. Gaxly Rudderbust
won’t publish hearsay, but he’s not above sharing
it inside his network of con dants. Seeking
information from Rudderbust grants Katie a +5
bonus to Intelligence (Investigation) checks made
regarding the city’s nobility.
Fishing Expedition. Katie can convince
Rudderbust to print bits of information (although
never anything libelous) she wants the nobility to
see. Since nearly every noble house is a subscriber
to the broadsheet, it’s almost certain that
interested parties will become aware of what was
printed.
SEVENTH LEVEL
Hit Points 36
Interrogator
Katie gains pro ciency in the Deception skill, and
is particularly adept at disguising the true intent
of questions she asks. Katie doubles her
pro ciency bonus when making a Charisma
(Deception) check to conceal her own knowledge
and motives while asking a question
Katie also learns zone of truth. Once she casts it,
she cannot cast it again until she completes a long
rest.
EIGHTH LEVEL
Hit Points 40
Ability Score Improvement
Wisdom 14 (+2)
Naturespeaker
Katie’s tutelage under Fala Lefaliir is yielding
impressive results. Katie learns speak with animals,
and speak with plants. Once she casts one of these
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spells she cannot cast that spell again until she
completes a short or long rest.
Katie’s uncanny naturalistic connection to the
weave hasn’t gone unnoticed by the Emerald
Enclave. Katie is welcome at Phaulkonmere (see
chapter 2 of Waterdeep: Dragon Heist), where
demigod Jeryth Phaulkon has taken a personal
interest in her. Katie can petition Phaulkon to cast
druid spells on her behalf. The DM determines
which requests are granted.
NINTH LEVEL
Hit Points 45
Ethereal Residuals
Once per day, Katie can extend her awareness to
remnants from her current surroundings left in
the Border Ethereal. When she does so, Katie can
sense if the following happened in the last 24
hours:
• A violent act occurred at a location, but not
the perpetrator, victim, or means of violence.
• A spell was cast. Katie can sense the location
of the caster, the point of origin and area of
effect of the spell, and its school of magic, but
not the name of the spell or the identity of its
caster or anyone affected by it.
• A lock was opened, and whether by key or
thieves’ tools, but not the identity of anyone
opening the lock.
The awareness lasts for 10 minutes or until
Katie loses concentration, as if concentrating on a
spell. Once Katie uses this feature, she cannot do
so again until she completes a long rest.
TENTH LEVEL
Hit Points 49
Surveillant Savant
Katie can hold an impressive stakeout. When she
picks a spot to take cover, Katie gains advantage
on Dexterity (Stealth) checks to remain hidden
there. For the next 12 hours, Katie can remain
attentive, silent, and motionless, and has
advantage on Wisdom (Perception) checks that
rely on hearing or sight.
Katie also learns see invisibility. Once she casts
it, she cannot cast it again until she completes a
long rest.
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 CREATING MYSTERIES SUSPECTS AND CLUES
Give your detectives a number of characters upon
Adventures from a hardcover book won’t hold a
which to cast suspicion and accusation, and the
candle to mysteries you dream up if you keep these
means to incriminate or exonerate them. The
eight factors in mind.
setup or discovery of the crime should provide
THEME the adventurers a few characters to speak with
and a few locations to visit. Each could branch
The backdrop against which the adventure is set
slightly, and it’s okay if there are a few dead ends,
is the element beyond the crime itself that creates
but at some point the characters should nd
the plot of your mystery. A good theme makes
multiple clues pointing in the same direction.
each mystery unique and interesting, as opposed
to a rote formula to be followed. Ideas for themes
could include a particular monster, an event such
ACTION
In a mystery-style adventure, the party will be
as a festival or holiday, a unique location, the
doing plenty of exploration and social interaction.
workings of a particular trade, a religion or cult,
Don’t forget about the third tier! Since the villain
or anything unusual and colorful. Once you have
is actively working to thwart the heroes, the
decided on a theme you nd interesting, it will
characters should be put into some sort of con ict
inform all the other aspects of your mystery.
or danger. It could be combat, although if it’s with
MOTIVATION the villain and or perpetrator rather than their
henchmen, be sure to provide a satisfying
The best mysteries provide the adventurers
conclusion aside from vigilante justice. A chase
motivation above and beyond merely the allure of
scene (see “Chases” in chapter 8 of the Dungeon
reward or their sense of duty. Perhaps the crime
Masters Guide) could lead to or from combat, or to
or the methods by which it were carried out are so
an important location or clue. Perhaps the villain
morally repugnant that the characters’ outrage
springs a devious trap (see ”Complex Traps” in
compels them to seek justice. Some aspect of the
chapter 2 of Xanathar’s Guide to Everything.) At
crime—or a clue found along the way—could tie
some point in the mystery adventure, roll
into a character’s backstory, invoking the “Okay,
initiative.
now it’s personal” trope. When the crime
connects to the campaign’s overarching plot, a
nemesis, or the adventurers goals, the push to
TWIST
An additional layer revealed near the end of the
solve it piggybacks on and even exacerbates
adventure on top of what has already been
existing drives.
discovered can be satisfying, but approach with
VILLAIN caution. A twist should never negate what the
characters have discovered and accomplished,
Just as the adventurers are heroes with
and should t clues that were presented (even if
exceptional abilities, so must the villain be
those clues were vague and missed.) Not every
exceptional, and capable of thwarting the heroes.
mystery requires a twist. If it feels gimmicky
Coasting to victory, after all, never feels very
instead of satisfying, drop it.
heroic. The villain could be, but need not be, the
perpetrator of the actual crime.
JUSTICE
METHOD AND MOTIVE The resolution of the mystery should involve a
sense that the characters’ undertaking had some
A mugging is less interesting than a
sort of consequence for the perpetrator and/or
pickpocketing, which in turn is less interesting
villain. Even if, for ongoing plot purposes, the
than kidnapping and mind erasure. Greed and
bad guy “gets away,” the players should be able
hatred are core motivations for crime; the more
to take satisfaction in knowing that they dealt a
unusual the speci cs, the more interesting the
setback or in icted some sort of cost.
mystery.

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 MYSTERIOUS LOCALES
A great mystery should be set against an
interesting or unusual backdrop. The City of
Splendors more than lives up to its nickname,
with a perfect setting for your mystery adventure
lurking around every corner. Here are some
examples from each ward of the city.
CASTLE WARD
As the center of power of Waterdeep, the Castle
Ward suits mystery themes of political intrigue.
Heavily guarded by the City Watch, murder by
poisoning or grift by long con are more likely
than a back-alley stabbing or mere snatch-and-
grab robbery.
The Palace of Waterdeep
Before the palace lies a spacious, well-landscaped
courtyard surrounding a slim spire known as
Ahghairon’s Tower. The legendary wizard sealed
it tight with invisible shielding prior to his death,
but there is one creature that lurks between the
magical barrier and the impregnable stone
structure behind it. The skeleton of Biliona
Fallimant, a wizard who long ago was only
partially successful in her breach of the fortress in
search of Ahghairon’s hidden magical secrets, is
doomed to undeath here. She will tell her tale of
woe to any visitor with the patience for her long-
winded ramblings, and could serve as an
eyewitness to nefarious plots hatched within
earshot.
The general public is allowed limited access to
the Palace of Waterdeep through the Main Gate,
which lies beyond that courtyard. One
immediately notices the incredible acoustics of
the cavernous entry hall, domed by smooth
polished marble. Standing in any particular spot,
a whispered conversation can be heard echoed
from a paired position across the vast space.
The massive stone stairway covered in lush
velvet carpeting to the left leads up to the court of
the Masked Lords. The archway to the right leads
to the bustling of ces of the city city clerks. Set in
the hall of the clerks is a huge stone table
featuring an intricately detailed scale model of the
city, from the harbor all the way to the gate to the
north of the Field Ward. A discrepancy between
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the model of record and the actual place could
serve as the clue that cracks your case wide open.
Phalantar’s Philtres
By far the largest business challenge faced by
Phalantar Orivan is the proper balance between
obscurity and notoriety. His namesake shop on
the Street of Bells near Cat Alley is widely known
to have the widest selection of rare herbs, oils,
and bric-a-brac used as components in wizardry,
alchemy, and arti ce. This is all a front to his more
lucrative backroom dealings in poisons, drugs,
forbidden magic, and the fencing of stolen goods.
In order to maintain good trade in the latter, he
strives to be a whispered name in the
underworld, while remaining out of view of the
City Watch (many of whom are on the take). His
secret is subtle branding. All the illicit goods that
pass through Phalantar’s hands are imprinted—
visibly or otherwise—with a tiny stylized ph
marking. If anyone in his shop verbally mentions
this brand mark, a hidden glyph automatically
casts a modify memory spell on everyone in the
premises except the shopkeeper. The victims
retain no memory of the marking or that it
brought them there; instead they only have the
sense that Phalantar is someone important who
can help them. Phalantar keeps no written
records, but has an impeccable memory. Keeping
the secrets of his shady clientele best serves his
sel sh business interests… until it doesn’t.
Mother Tathlorn’s House of
Pleasure and Healing
Far Travelers often feel a jolt of culture shock
when rst learning of the Waterdhavian festhall
(not least because they often rst arrive expecting
a “feast hall”). Prudishness is not part of the
progressive metropolitan ideal. Waterdeep’s
Festhalls are adult playgrounds, and Mother
Tathlorn’s, set in the hill below the Palace just off
Waterdeep Way, is the nest of them all. Yes, the
Realms’ oldest profession is practiced here. In
Waterdeep, that profession is considered a
legitimate one and its practitioners nd
themselves with far better working conditions,
pay, and respect than those in locales where the
trade is pushed into the underground. However,
not all or even most of what goes on here is
8
 beyond PG-13. Practically any form of
entertainment, comfort, relaxation, or indulgence
can be found in the festhalls of Waterdeep, and
Mother Tathlorn can accommodate nearly all,
providing the most opulent of experiences to the
wealthiest of clientele. Despite the culture’s
openness, discretion is still provided for those
who desire privacy. Everything from expressing
strange proclivities to healing major wounds from
sources unspoken are reason for Waterdeep’s elite
to trust in the House’s delicacy.
The Prowl
In the center of the block bounded on the sides by
the Street of Silver and Warrior’s Way, and Bazaar
and Selduth Streets to the north and south, is a
curving alley known to be the murder capital of
the Castle Ward. The Prowl claims a small
handful of lives in any given year, the necks of its
victims scarred with deep necrotic indentations of
skeletal hands. The undead killer magically
evades all the skilled wizards and clerics who
have come to dispel, vanquish, or capture it. Even
attempts at containing it seem fruitless, as any
barrier to the alley—be it physical or magical—
disintegrates within hours. As such, the
alleyway’s entrances feature large warning signs
enchanted with alarm and magic mouth spells to
dissuade anyone ignorant of the danger. When a
poor soul turns up dead here, the mystery is not
the identity of the killer, but how the victim could
have come to be in danger’s way.
CITY OF THE DEAD
Sir Ambrose, a knight of Kelemvor, works
tirelessly overseeing the protection of
Waterdeep’s large cemetery-cum-parkland.
Tirelessly is probably the wrong word, as
Ambrose seems perpetually tired due to his dusk-
till-dawn watch schedule—and he has the
demeanor to match.
The knight watchman has a pet faerie dragon,
that perches upon his shoulder when it’s not out
spying on his behalf. A family crypt, it turns out,
is a useful venue for the nobility to meet with the
shady types tasked with carrying out various
political schemes, and the faerie dragon is adept
at eavesdropping on these conversations.
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Ambrose himself rarely bothers with criminal
issues, as he is kept rather busy with the
necromancy problem.
DOCK WARD
When one imagines crime in Waterdeep, the mind
invariably descends to the Dock Ward. To those
from ports unknown hearing the tales of
returning sailors, the rough edge on the harbor is
the city itself. Brawling drunken sailors and
smugglers brawling with drunken merchants
who brawl in the streets. And sticuffs to boot.
Though the rowdiness is memorable, it’s nowhere
near as out of control as the stories say. The City
Watch makes sure of that, with patrols in this area
more frequent (and staffed by larger and more
experienced street brawlers) than anywhere else
in the city. Despite the rough types that the hard
labor professions here attract, raw capitalism
keeps the peace, at least as far as the continued
ow of goods is concerned. The harbor is the
engine of Waterdeep’s wealth, and the wealthy
know to protect it.
Helmstar Warehouse
For generations, no business in the Dock Ward
has been transacted without being touched in
some manner by the Helmstar clan. Completely
absent from high society, the Helmstars are part of
what those in the know refer to as Waterdeep’s
“shadow nobility.” No attendance of balls in
fancy garb, just hard deal making is the prospect
of this family. Their current matriarch is Verleiha
Helmstar, a severe woman with short cropped
hair of jet black that matches her eyes. She
currently resides with her partner Jheldessa
Kastonoph, chief captain of the Master Mariner’s
guild. Despite her intimate relationship with the
guild leader, Helmstar is also openly known to be
the propping up the rival Guild of Watermen.
Although no evidence has been presented to
support the supposition, many believe that the
Helmstar family has secured a hereditary position
as a Masked Lord... so long as their rule over the
Dock Ward remains without serious challenge.
 Dock Ward Brawling

WATEREEP MYSTERIES 10
 Serpentil Books
and Folios
The Great Library of Candlekeep is the North’s
shining beacon of open truth and honorable
scholarship. Jannaxil Serpentil’s unassuming shop
on Book Street stands in opposition as the
ruthlessly capitalistic exploitation of the written
word and the power it holds. Serpentil, a miserly
and frigid man, is an accomplished scholar and
wizard who views the accumulation of
knowledge as a tool for self-enrichment.
Everything from maps and sea charts, to rare
magical tomes, to personal diaries and letters of
Waterdhavians noble and low can be had here for
the right price. Serpentil also buys such papers,
all at a fraction of market value—and much lower
if Serpentil suspects the item to be stolen. The
wizard-scholar will never directly voice that he’s
playing the fence, but he almost always seems to
somehow know when it is the case.
If your mystery is staying “on-book,” so to
speak, there’s a good chance that book can be
found on Serpentil’s dusty shelves.
Three Pearls Nightclub
Nestled on Pearl Alley behind Snail Street is the
one of the greatest stages of entertainment in all
the Realms. This destination for performers draws
a new variety of acts each night, and has served
as the launchpad for the careers of countless
famous musicians, comics, minstrels, and
circuses. The massive room features low sitting
benches on a oor that gently slopes downward
towards the stage, and is anked on all sides by
counters hawking ale, wine, and tapas. On as
many nights as possible, as often as thrice a
tenday, the nger snacks include fried bits of
exotic monsters. With the variety of food and
entertainment vast and rarely repeating, it’s a
good bet that when you hear a friend brag of
having eaten grick skewers while a hand-stand-
walking sneber in juggled with her feet, that the
friend was surely the Three Pearls. With a bit of
sleuthing, it shouldn’t be too dif cult to
determine the speci c night.

Any given evening at the Three Pearls

11 WATERDEEP MYSTERIES
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A constant shadow looms over the Field Ward
FIELD WARD
Refugees from catastrophes throughout the North
live in squalor, packed into a shanty town
between the city’s northern border and outer
defensive perimeter. Along with poverty comes
lawlessness, which the City Watch chooses to
ignore completely. Travelers can pass safely
through the Troll or North Gates thanks to the
diligence of the City Guard, but they provide no
protection to those residing in the City’s Shame.
Crimes of want, opportunity, and passion are
common here. The Field Ward is also a popular
dumping ground for those inside the city who
run afoul of the Xanathar’s Guild or Zhentarim.
An unconscious form left in a Field Ward
alleyway will soon be stripped of their
possessions.
NORTH WARD
Home to the city’s lesser nobility, of which there
are a surprising amount, the North Ward seems
quiet and unassuming until one visits
accompanied by an insider.
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The Gentle Mermaid
If you nd the outside of this renovated manor
house to be offensively ostentatious, you’ll be all
the more wounded after passing through the coat
check. Although the lush decor, featuring soft,
shaggy red carpeting and enchanted crystal
chandeliers, is of their grandparents’ era, this
opulent gambling hall has been taken over by the
fashionable under-30 crowd of nobility in recent
years. Their preferred dice game is a high-
variance, low-skill affair, which prevents any one
player from winning too much of their peers’
parents’ gold. For the young and wealthy seeking
a mate—for a spouse or for the night—this club
currently stands as the place to see and be seen.
Galas de Villas
The Grand Gala of House Hawkwinter and the
Roaringhorn’s Roaring Horn are the North
Ward’s social events of the year, followed closely
by balls hosted by the prominent Than, Gralhund,
Tarm, Amcathra, and Margaster families. As the
North Ward is home to much of Waterdeep’s
nobility, lesser but still well-attended galas are
held frequently with each notable family hosting
at their own villa. Listed roughly from north to
south, you’ll nd parties throughout the year at
the Villas of houses Anteos, Phull, Snome,
Crommor, Piiradost, Thunderstaff, Talmost,
Sultlue, Cragsmere, Kothont, Lanngolyn,
Ulbrinter, Jardeth, Maerklos, Nandar,
Stormweather, Durinbold, Estelmer, Majarra,
Agundar, Hunabar, Thorp, Lathkule, Kormallis,
Adarbrent, Phylund, Zun, Hothemer, Ilvastarr,
Wands, Gost, and Helmfast.
Known collectively as the Galas de Villas du
Nord, these affairs are scheduled to never
overlap, necessitating a frequency of better than
once per tenday! The most exclusive families tend
to host only the most exclusive guests, but
merchants of notoriety or even adventures pad
out the guest lists of the less desirable affairs. The
primary work of these parties is gossip. As the
houses vie for their place in the pecking order,
rumors and lies are readily spread. Although
business is never carried out during the
festivities, the nobility readily take advantage of
the opportunity to make contacts and schedule
future closed-door meetings.
12
 Frewn’s Brews
The nest ales in Waterdeep, and even perhaps in
all of the Realms, are brewed in Trollskull Alley,
just below Saerdoun Street two blocks east off the
High Road, by a pompous man of little business
sense. Emmit Frewn’s twofold secret to success is
impeccable sanitation and an uncanny knack for
breeding highly specialized strains of yeast. His
taproom is a destination, as Frewn stubbornly
refuses to sell barrels wholesale to other taverns,
Most take their delicious brew to-go in 1 gallon
containers, as the accommodations are as
unpleasant as the management. The few regular
bar ies are rough types who are rumored to be
agents of the Xanathar’s Guild keeping an eye on
a nearby adventuring company backed by the
infamous writer Volothamp Geddarm. The
brewery produces three varieties: Frewn’s Black, a
stout with a luxurious mouthfeel; Frewn’s Red, a
full-bodied affair constructed from numerous
speciality grains grown in the farms of Undercliff;
and Frewn’s Blonde, a hop-bomb, light in color
and body, featuring fruit aromas that put ne
wines to shame. Due to their differing gravities,
the ales, if poured carefully, can be layered atop
one another in a single glass. Frewn absolutely
hates this. Anyone doing so in the taproom is
immediately ejected, and any patron lling
containers to be taken off premises is made to
sign a non-legally binding form attesting that they
will not sully the brewmaster’s perfect creations.
Lately, Frewn has been bragging that he is close to
perfecting a brewing technique that would render
any such blends of his ales undrinkable.
SEA WARD
Although retaining a few vestigial connections to
the sailors and traders who rst settled in the
area, the Sea Ward now smells not of brine but
rather wealth and power. It is heavily patrolled
and largely free of street crime. One doesn’t have
to dig too deep, however, to nd the
underground.
13 WATERDEEP MYSTERIES
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Tespergates
Every Tenth Day, rain or shine, the noble Tesper
family opens their gates to all folk for an all-night
bash centered around a tournament. The game is
always unique and is always announced only at
commencement of the event. It is usually a team
affair, and always incorporates some sort of hard
body contact. Although healers are kept on the
premises to tend to the inevitable concussions and
broken bones, many competitors do carry home
grudges that they may hold for a lifetime. The
villa is known to be haunted by a pair of Tesper
sisters, Yulhymbra and Silpara, now centuries
dead. The two make their fun by magically
coaxing dark secrets from those exhausted by the
night’s competition. Less well known is that
Silpara is romantically involved with Nleera
Tarannath, a mage who passes along the secrets
she learns to the Harpers.
The Fiery Flagon
Imagine the Dock Ward’s dingiest dive bar. Now
ll it full of pirates dressed in nery and dining
on haute seafood cuisine. Put it below a row of
tiny shopfronts across from the House of Inspired
Hands on Seawatch Street and you have the Fiery
Flagon Tavern. Its proprietor, Ulscaleer Anbersyr,
is an old retired pirate who manages to keep out
both the rifraff and the nobility (the former by
pricing, the later by decor and decorum). The
patrons are rough sailors with booty to spare. The
meals are splendid, and so are the opportunities
—Anbersyr serves as both fence and out tter.
Trade is rumored to be facilitated by a heavily
guarded tunnel on the Flagon’s sublevel which
leads to the River Saugauth in Undermountain.
Anbersyr is quietly known as Waterdeep’s only
reliable supplier of serviceable quantities of
smokepowder.
Gondwatch Lane
The Sea Ward is home to numerous temples and
shrines, but only one, the House of Inspired
Hands, warrants a back alley frequented by the
curious and devious alike. When an acolyte of
Gond unveils an Inspired Creation, it is done so
out back for safety purposes. Very few rst
iterations get things exactly right, and explosions
inside the temple are frowned upon. Word of an
 experimental deployment spreads quickly, and
the alley lls with spectators. Failures are cheered
more loudly than successes. Back-alley deals are
also conducted here. Although the religion frowns
upon inventions with no practical purpose,
there’s individual disagreement as to what ts
that de nition. Some devotees fund their research
by selling inventions that clearly have no merit
outside of unscrupulous practices.
SOUTHERN WARD
Don’t let this most ordinary-appearing of
Waterdeep’s Wards, with common folk going
about common business, fool you into thinking
that the Southern Ward lacks intrigue.
Shalara’s Sanctuary
In recent decades a new tradition has sprung up,
in which young people entering into a new
chapter in their lives—adventuring, taking on a
trade, traveling, and so forth… but in particular
seeking romance—visit Anchoret’s Court and
drink the crisp water from the public well there.
It’s said that the aquifer servicing this well draws
deep down into Undermountian, where it
accumulates a luck-providing magical aura.
These rumors are intentionally spread by
Shalara Malarrkin, who lives in an unassuming
brick home at the Court’s northern entrance. The
well water is enchanted by the aged wizard who
has dedicated her life’s work to preventing young
folk from suffering the same fate that befell her.
Early in her teenage years, Shalara left her
home in Amphail to apprentice under the potion
master Kappiyan Flurmastyr. A brass plate
bearing his name still adorns the door to her
home sitting across from the well. Kappiyan was
a kind old wizard who treated Shalara quite well.
She adored him, and the two were married when
she was merely 17 years old, her master and then
husband nearly forty years her senior. For twenty
years they were partners in marriage and
research. It was only upon Kappiyan’s death that
Shalara discovered her former mentor’s deceit.
She had never loved the man, having the whole
time been under the in uence of a magical love
charm, the philter of which had been steadily fed
to her over the years.
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With this revelation, Shalara took it upon
herself to protect others from having their
autonomy magically violated. The well in the
courtyard is continuously injected from a potion
brewery located in her cellar, which, fed the
proper reagent, is self-sustaining. Anyone
drinking from the well gains resistance to
enchantment magic for a tenday and any
charmed condition on them immediately ends.
Shalara is similarity quiet yet effective in more
targeted efforts to prevent the use of enchantment
magic. She is currently working to disrupt the
efforts of a humanoid traf cking ring based out of
Amn.
Aurora Logistics HQ
After the spellplague, competitors couldn’t keep
up with the modern approach taken by Aurora’s
Whole Realms Shop—now rebranded as simply
“Aurora.”
Leaning hard into their infrastructure of
teleportation portals, the mega-retailer came to
dominate the Realms by dint of putting nearly
any common item on your doorstep within two
days.
The value engine behind the business is data
collection. Aurora always seems to know exactly
what you want to buy, even before you do. With
over 70 percent of Waterdhavian households
subscribing to the Aurora Prime service, and
more than half of those setting timers on, placing
orders with, and generally thoughtlessly chatting
in front of Aurora Reverb stones, Aurora possesses
a vast knowledge of the populace.
Aurora continues to operate their old catalog
counters in each of Waterdeep’s wards—partly as
pickup spot for those wary of porch pirates, but
moreso enabling their new two-hour city-wide
delivery service. The Southern Ward location on
the Way of the Dragon has the additional honor of
hosting the wizards who make Aurora’s retail
magic possible.
Although both parties refuse to comment on
the matter, it’s widely believed that in exchange
for allowing Aurora’s magical operations in the
city, the Watchful Order of Magists and Protectors
has unfettered access to Aurora’s proprietary
data.
14
 The Blacklock
With the recent resurgence in fame of the Mad
Mage of Undermountain, Hallister Blackcloak, the
popular name—re ected on modern maps—is
Blackcloak Alley. Longtime residents still refer to
it as Blacklock Alley, insisting it is named for the
strange obelisk standing in its center.
Perhaps both are true. Oghmatic scholars are
fascinated with the artifact. Their current thinking
is that the waist-high pillar with the strange hole
through the center is actually a spire of a temple
to Lathandar that sank when Hallister formed his
infamous dungeon below.
The hole in the Blacklock has strange properties
that are not yet fully understood. It heals the
wounds of limbs placed through it, but seemingly
only for the pure of heart. Some nd that objects
placed in the hole disappear, while others see the
object emerge from the other side enhanced in
some way.
The fact that so many knives and daggers
recovered in expeditions launched from the
Yawning Portal are cursed with the stench of
murder certainly raises suspicions.
For a tenday of adventure with the
Dungsweepers featuring more than 35 encounters
check out Dung Work on the Dungeon Master’s
Guild. Purchasers of Waterdeep Mysteries can
contact the author to obtain a complementary
copy.
Inn of the Dripping Dagger
The comfortable accommodations and excellent
menu aren’t mysterious, and neither is the
proprietor. Filiare seems to be known, liked, and
trusted by all. The retired mercenary loves telling
the stories of his sellsword days, and is eager to
recruit any hired ghter he can nd.
As a man of honor, Filiare has no stomach for
his mercenaries engaging in illegal behavior of
any kind, even as accessories. He also steadfastly
refuses to cooperate in any of cial investigations.
Off the record, however, Filiare is happy to
gripe about hires who have disappointed him. He
views himself as enforcing an unof cial blacklist
of such condottieri by doing so.

TRADES WARD
Commerce of all kinds is the de ning
characteristic of the Trades Ward. Nearly every
trade is practiced here, if you look hard enough
for it. Just because Waterdeep doesn’t allow
guilds dedicated to shady dealings doesn’t mean
that they aren’t going on.

Cole’s Dungsweeper Crew

This motley corps isn’t so much a location in the
Trades Ward so much as a proxy for the entire
Ward itself. Cole and his associates Jasper and
Faith know about all the dung going down. Any
of cial relationship needs to be arranged though
guildmaster Zulgoss Helberad, who operates out
of Muleskull Tavern in the Dock Ward—and
you’d better come with a well-placed reference.
It’s against guild rules for Cole to take payment
directly, although he’s pretty relaxed about using
his crew’s resources in exchange for favors—
either explicit or to be arranged at a future date.

Jasper obligingly waits to sweep some small dung

15 WATERDEEP MYSTERIES
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Filiare has no stomach for his mercenaries engaging in illegal behavior

WATEREEP MYSTERIES 16
 MAGIC ITEMS
Costume Headband
Wondrous Item, Uncommon
Upon placing this headband on your head, you
change in appearance as though under the effects
of a disguise self spell. The nature of the illusion is
determined at the time the headband is created.
The illusion remains until the headband is
removed. To discern that you are costumed in an
illusion, a creature can use its action to inspect
your appearance and must succeed on an DC 12
Intelligence (Investigation) check.
Costume headbands are commonly used in
upscale theater productions in Waterdeep,
although they are looked down upon by the elite
producers, such as the Lightsinger Theater, who
consider them a “cheap affront” to proper
costuming.
Ring of Altering Self Disguise
Wondrous Item, Very Rare
While wearing this ring, casting the disguise self
spell invokes additional transmutation magic. All
of the illusionary effects of the spell become a
physical transformation, as though you had cast
the alter self spell.
If you are attuned to the ring, the duration of
the spell is inde nite, until you decide to dismiss
it, and does not require you to maintain
concentration on it.
Guardian Bracelets
Wondrous Item, Rare (Requires Attunement)
This matching pair of bracelets are made of
adamantine and adjust to the size of the wearer
when attuned. While wearing either of these
bracelets, you can use an action to cast sending
from it. The target is the wearer of the matched
bracelet. Once sending is cast through a bracelet it
can’t be cast again from that bracelet until the
next dawn.
The pair consists of a guardian bracelet and a
ward bracelet.
Guardian bracelet. When you attune to the
guardian bracelet you determine a boundary for
17 WATERDEEP MYSTERIES
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the matching ward bracelet. Such a boundary can
either be a xed distance from a speci c point you
are familiar with (e.g., 1 mile from home) or an
arbitrary boundary that you have traversed (e.g.,
the walls of a city).
The guardian bracelet has 3 charges, and it
regains all spent charges at dawn. While wearing
the guardian bracelet, you can use your action to
expend a charge to determine the position of the
ward bracelet. When you do so, you learn the
current position of the ward bracelet if it is a place
you are familiar with. Otherwise you learn the
last location of the ward bracelet that you are
familiar with and the time elapsed since it
appeared there.
Once per day, you can use the guardian
bracelet to cast locate object, targeting the ward
bracelet.
The guardian bracelet vibrates softly to alert
you when:
• The ward bracelet leaves the speci ed
boundary.
• The ward bracelet is removed or its wearer’s
attunement to it ends.
• The creature attuned to the ward bracelet falls
unconscious, other than falling asleep.
When you end your attunement to the
guardian bracelet, the wearer of the ward bracelet
automatically ends their attunement to the ward
bracelet as well.
Ward bracelet. After you attune to a ward
bracelet, you cannot voluntarily remove it or end
your attunement to it without the use of a remove
curse spell or other magic.
The ward bracelet vibrates softly when you
come within 50 feet of the boundary established
by the the guardian bracelet, and the ward
bracelet vibrates violently, easily noticeable by
other creatures, when you exceed the boundary.
Guardian Bracelets are commonly used by the
courts, overbearing spouses, and protective
parents. Some wealthy nobility wear a ward
bracelet tied to their personal bodyguard as
guardian.