Table EngineAdventure Keepers · LIDM

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Adventure Keepers · A Free Table Keeper

Where the Road Ends

Four wildernesses. Four encounter tables. Four fights worth having. Rollable in your browser, free, and yours to keep.

A cart road ends in wild grass at a leaning stone cairn; forest, mountain and grey sea beyond

At a glance — any wilderness leg of any campaign · written for four 3rd-level characters (every framed encounter carries its own math; scaling for levels 1–10, parties of 3–6) · a rolled row plays in 5–20 minutes; each framed encounter runs 30–45 minutes · every named check is DC 10, 13, or 15, and failure always moves the scene somewhere.

An Adventure Keepers interactive toolkit · 5e-compatible (SRD 5.1)

The land wants things

Every DM has said “you travel three days” and felt the table deflate. The usual fix is a random encounter, and the usual random encounter is “roll initiative, it’s wolves,” which is worse than nothing: a fight with no question in it, eating forty minutes to decide what everyone already knows.

The tables in this Keeper are built on a different rule: nothing steps out of the trees without a want. The wolves are driving, not hunting. The bandits are mid-crime and open to a better offer. The thing at the ferry crossing wants what it has always wanted, and the horror is how reasonable it sounds. Every row gives you a creature, a situation, and a fork — a decision the players make while the encounter is still moving. Fight is always on the menu. It’s just never the only thing on it.

What the party can do
  • Roll in the deck: open DM Tools → Random Tables — all four biome d10s are loaded. Or hit any inline roll chip, like this one: .
  • Rows 1–9 are live encounters you improvise from the seed. Row 10 is framed — the full scene, written out under its table, ready to run cold.
  • The clocks are loaded too: the Weeping Stair climb and the tide over the Teeth are preset in DM Tools → Scene Clocks. The combat tracker carries every framed encounter’s roster.
  • Player Mode (topbar, or the p key) hides everything GM-facing — safe to cast to a TV.
A rolled 10 never repeats — it continues

If the die hands you a framed encounter a second time this campaign, you haven’t rolled a rerun. You’ve rolled a recurring character. Maren remembers. Hob keeps accounts. The sisters know the shape of you. Run the reunion.

The companion to the free Wilderness Pack

This Keeper has a sibling on the site: The Wilderness Pack, free at longislanddungeonmaster.com/downloads. That one is the quiet days — the watch sounds, the weather, the strangers, the camp that won’t settle. This Keeper is for the other days. The Pack asks what’s out there? This one answers it’s here.

The forest

The tools begin long before the camp does.
The tools begin long before the camp does.

The forest’s want is simple: everything in its place. The trouble is that everything already has one, and a party of armed strangers hauling iron and fire down a game trail is a moved piece. Forest encounters are territorial. Whatever you meet was here first, thinks in boundaries, and reads the party as either trespass or opportunity. Play distances short, sightlines shorter, and let the players hear things a full round before they see them.

What steps out of the trees — d10
d10The encounter
1Three wolves, not hunting — herding. They flank the party at a trot, snapping at heels, bending the march off the trail — driving the party toward the thing that eats what wolves won’t. Go where they push, or break through and find out what they’re so afraid of.
2A black bear wearing a saddle. Trained, calm, and lost. It knows one command word, stitched into the saddle blanket. The bandits who lost it are half a day behind and want it back more than they want a fight.
3An ettercap’s larder. Two poachers hang alive in web sacks over the trail, arguing in whispers about whose fault this is. Cut them down and their argument becomes the party’s problem: they were poaching for someone much worse, and the quota is due. The ettercap is closer than the whispering suggests.
4Four bandits robbing a wedding. The procession was walking to the chapel in the next village. The groom, hands up, is loudly offering the bandits less than he’s wearing. The bride is counting the bandits’ mistakes. Whoever the party backs, somebody’s family remembers.
5Fresh web across the only bridge, strung at face height, and no spider in sight. It’s under the planks, and it has learned that the web doesn’t catch travelers — the bridge does.
6A sprite war over a dead oak. Two banners of sprites, a dozen a side, drawn up in the branches. Both sides claim the party as the reinforcements their prophecy promised. Refusing both is also taking a side.
7An awakened tree standing where the road was yesterday. It is not hostile. It is hiding, badly, from an axe it can hear and the party can’t yet. It will move for anyone who promises to deal with the axe.
8A lord’s huntsman, clearing the wood. A scout with a writ, two dogs, and a torch, burning squatters’ camps ahead of a survey. The writ is real. So are the squatters’ children, watching their winter stores go up. He’d rather the party moved them than he did.
9Everything with legs, going one way. Deer, foxes, birds, all crossing the trail at a run. Behind them, an owlbear at the tree line, head down, snuffling a scent — theirs, or the party’s. It hasn’t seen anyone yet. Freeze, flee with the animals, or take the one free round.
10The Warden of the Cut. The framed encounter — written out in full in this Keeper: the read-aloud, the GM truth, the choice, outcomes, and scaling.

Roll it here: — or in DM Tools → Random Tables.

Framed: The Warden of the Cut

Read aloud

Long before the logging camp comes into view, the tools begin. Axes, saws, iron wedges, a full timber chain — all of it hung from the branches overhead like game left to bleed. The newest thing hanging is a pair of boots, laced together, still swinging. High above them, wedged in the crook of a big oak, a man in a foreman’s leathers hugs the trunk and does not call for help. Somewhere upslope, a woman’s voice is talking to the trees, low and even, the way you’d talk to horses before bad weather.

What’s really going on

The camp below is cutting a firebreak on a lord’s writ. Maren of the Cut has spent twenty years keeping this slope, and she knows what the surveyor didn’t ask: the big oak’s roots are the only thing pinning the hillside above the village. Cut it, and the spring melt brings the whole slope down on forty roofs. She has tried words. Now she hangs tools, and this morning she treed the foreman. She is right about the slope and wrong about everything she’s doing, and she half-knows it — run her as a confession, not a fight. She wants to be stopped by someone who believes her.

The choice

Back the camp (bring her in, the cut proceeds), back her (stop the cut and answer for the writ), or do the thing nobody upslope or down has done: check.

What the party can do
  • Read the hillside — an hour and a DC 13 Wisdom (Survival) check . Success: the erosion scars, the leaning fence-posts, the buried boundary stone — Maren is right, and the proof is showable. Failure: the party finds the signs but not the shape of them; the foreman’s surveyor can be made to walk it, if the party gets him down and keeps Maren back while he works.
  • Talk her down without proof — DC 15 Charisma (Persuasion) . Failure doesn’t end the parley — it ends her patience with parley, and the boots come down on a cut rope while she walks away. With proof in hand, no check: she stands down and stands beside them.
  • Fight — Maren opens with entangle, not damage, and yields below half. She is trying to win, not kill.
Budget (four 3rd-levels; thresholds 300/600/900/1,600 adjusted)

Maren (druid, 450 XP) + 2 wolves (50 each) = 550 raw ×2 for numbers = 1,100 adjusted — past hard, shy of deadly — and it plays a tier softer than the math because she opens with entangle and yields the moment she’s below half.

Outcomes

Proof moves the cut and makes the party a friend on this slope for life. Backing the camp gets the writ’s bounty and, come spring, a village that remembers who was here. Backing Maren without proof makes them outlaws with a clean conscience. Any path where the foreman comes down alive, he pays the party his own coin to keep the “treed by a tree-witch” part quiet.

What the party leaves with: the camp’s gratitude-purse or the writ-bounty (25 gp either way), and — if Maren walks away their ally — a knot of living wood granting advantage on Wisdom (Survival) checks anywhere under this forest’s canopy.

Scaling

Levels 1–2: no wolves; Maren alone, surrenders at half HP. Levels 4–5: four wolves and a second entangle. Levels 6+: don’t scale the fight — scale the stakes: the melt is this month, the village is bigger, and the lord’s surveyor is already dead in a gully (nobody’s fault; everyone’s problem). Party of 3: drop one wolf. Party of 6: add two.

The swamp

The toll hasn’t changed since anyone can remember: no coin.
The toll hasn’t changed since anyone can remember: no coin.

The swamp doesn’t chase anyone. It waits, and it charges for everything: dry ground, clean water, the crossing, the way out. Every creature in it has learned the same economy, which is why swamp encounters feel like negotiations even when they’re ambushes. Whatever the party meets wants a toll — meat, coin, help, truth — and the water decides who’s bargaining from strength. Keep the party wet, keep their feet uncertain, and price everything.

What the water gives up — d10
d10The encounter
1Three giant frogs, and one of them just swallowed the smallest pack in the party. Whole. They scatter in three directions through knee-deep bog, and the one with the rations and the map is the fastest.
2A stirge cloud rising off a sinking mule train. Five of them, fat and slow, and two drivers still in the muck fighting to cut the last mule free. Help means sharing the stirges’ attention. Waiting means watching the mule go under with its panniers.
3Two lizardfolk at a boundary of turtle shells on stakes. Not raiding — warning. In trade-pidgin and gesture: the deep pools are moving. Something has pushed them out of their own hunting water, and they’ll trade safe passage for help nobody else will give them.
4The log beside the third crossing-stone is a crocodile. It has learned the stones. Two locals lost this season, a posted bounty, and a widow who only wants the wedding ring back — it’s still on the hand.
5Two ferry lanterns at dusk, both holding still over the water. One is the ferry. The other is a will-o’-wisp that has learned the ferry’s light, its height, even its slow swing. The wisp’s copy is very good. The ferryman’s is the one that answers a shout — usually.
6Chimney tops above the waterline, and a bell. A drowned village, low-water season, and the sunken chapel’s bell rings once as the party passes — nothing natural pulls that rope. Swim for it and the belfry’s congregation wakes: two ghouls that have kept their pews for years, fed by whatever the bell brings.
7An ogre’s dam. He built it himself, log by log, for the fish pond. Upstream is drowning; downstream is drying; the trail is under three feet of new water. He is proud of the dam the way a child is proud, and he will fight for it — or trade it, for something exactly as good as a pond.
8A raft of fleeing families, poling the wrong way. Deeper in, following their hired “guide” — a bandit steering them to his crew’s island, where the fee goes up. He’s charming and plausible. The party knows this stretch of water better than his story does.
9A courier in a peat sink, holding his satchel over his head. Waist-deep and sinking slow, shouting an offer that goes up every minute. He thinks it’s mud that has him. The party can see the giant constrictor’s coils breaking the surface behind him. The satchel is worth more than he is, and the worst part is he knows it.
10The Ferryman’s Toll. The framed encounter — written out in full in this Keeper: the read-aloud, the GM truth, the choice, outcomes, and scaling.

Roll it here: — or in DM Tools → Random Tables.

Framed: The Ferryman’s Toll

Read aloud

The crossing is a rope strung bank to bank over black water, and a flat raft, and a ferryman in a hooded oilskin who was poling this stretch when your grandmother was young. Locals leave his toll folded on paper in a box on a post — written truths, signed — and don’t wait for him to come read them. Up close, under the hood, the skin is wrong — river-gray, drawn tight — and the smell is pond bottom. He raises a crooked hand, then touches his ear. The toll hasn’t changed since anyone can remember: no coin. One true thing, spoken aloud, per passenger.

Old Hob drowned at mid-river seventeen winters ago and did not let go of the rope. What came up is a ghast that still knows one thing: he is the ferryman. The post is the leash. Working the crossing is the only thing that keeps the hunger walking behind him instead of in front, and he has held that line for seventeen years by his own rules: passengers pay a truth, because he can smell a lie now the way the living smell rain, and lies are the one thing that snaps the leash. Two ghouls cling to the raft’s underside — liars, from over the years. He calls them his passengers. He is not proud of them.

The choice

Pay true, find another way across, or make it a fight on four feet of wet planking. The truth-toll is the scene: each character says one true thing out loud, and Hob knows. A safe fact is legal tender. A real one — something it costs the speaker to say — and Hob poles slower, and answers a question about the water, the road ahead, or the seventeen years, honestly.

What the party can do
  • Pay false — Hob stops the raft at mid-river and points at the water. He gives liars one chance to pay double — two truths — before the passengers come up.
  • Fight on the raft — any round the raft lurches (a ghoul boarding, a big hit, a shove), everyone standing makes a DC 10 Dexterity (Acrobatics) check ; failure means prone, or in the water on a second failure. Hob fights at the pole; the ghouls climb aboard at the ends of rounds two and three, not before.
  • The drowned ford — two miles of wisp-lit backwater and a DC 15 Wisdom (Survival) check . Failure isn’t lost — it’s the long way, after dark, through table row 5.
Budget (four 3rd-levels)

Hob (ghast, 450 XP) + both passengers (ghouls, 200 each) = 850 raw ×2 = 1,700 adjusted — deadly on paper (threshold 1,600). The design breaks that math on purpose: the multiplier assumes everything fights at once, and here round one is Hob alone, with one ghoul boarding at the end of round two and the other at round three. Run the boarding on schedule and it plays hard, not deadly; let them all start on the raft and it is deadly, and that’s on you. In the water it stops being a fight and starts being a drowning.

Outcomes

Pay true and the party crosses with a dead man’s honest answers, which is more than most oracles sell. Kill Hob and the crossing is theirs — and unmanned; within a month the ferry is gone, the ford claims a family, and the party hears about it. Cut the ghouls loose without killing Hob and he poles them across free, forever.

What the party leaves with: passage, whatever his answers were worth, and — if they deal fair — the toll-box: 40 gp in coins seventeen years out of date, and one keepsake from a liar that somebody, somewhere, is still looking for. Hook it to your campaign.

Scaling

Levels 1–2: Hob alone; the passengers stay under the raft unless blood hits the water. Levels 4–5: three passengers. Levels 6+: the fight was never the point — raise the toll: Hob wants one truth the whole party doesn’t already know. Party of 3: one ghoul. Party of 6: the raft fits four; splitting the party across two crossings is the scenario.

The mountain

The Weeping Stair, and the two shapes that ride the wind above it.
The Weeping Stair, and the two shapes that ride the wind above it.

The mountain doesn’t want anything. That’s the horror of it. Everything alive up here is squeezed against everything else alive by cold, thin air, and gravity, and every encounter is really about the same three things: the path, the shelter, and the fall. Fights at altitude are short and stupid; the smart creatures up here (and most of them are smart, or old) would rather charge a toll than bleed. Make the players feel the drop on every check.

What the height costs — d10
d10The encounter
1Goats first, then pebbles. A herd pouring down the switchback means something’s above. The party gets one round to pick shelter before the slide — and the wolves that started it arrive to find dinner conveniently pinned.
2A giant eagle, circling for an hour, lands ahead and speaks. Climbers on ropes are robbing her nest. The climbers are villagers, starving, after eggs that sell for a season’s grain. She will carry a champion up. She has not thought past that, and neither have they.
3A rope bridge, and a berserker halfway across it, coming the other way. He will not back up. Not for words, not for coin, not for the obvious math of the drop. It isn’t tactics. It’s the last thing he has, and everyone on both cliffs can feel it.
4Arrow slits in the cliff face, and one small voice. A kobold toll-gallery, offering “the safe price.” Their tunnel really does bypass the avalanche field — they’re not lying about that, and they are all, always, home.
5The horses scream first. A griffon, stooping out of the sun at the pack animals. It wants horseflesh, not people, and it will trade the fight for a mule if someone’s quick enough to cut one loose. At this altitude, that arithmetic is worth doing out loud.
6The only cave ahead of the storm, already denned. A brown bear, asleep for now, and the weather closing the question of “elsewhere.” Room for everyone, if nobody’s greedy about the dry spot — or one very bad wake-up.
7The signal-keeper’s fire, unlit. A scout tends the beacon line; someone paid him not to light tonight’s. He’ll say who, and for how much, if the party beats the offer. Below in the dark, whatever the beacon warns about is already moving.
8An orc procession, carrying their chief’s cairn-stone up. They ask — ask — the party to stand honor-watch: their numbers are thin, and the dead chief’s rival is coming to scatter the cairn. A night of shared watch beside orcs, or the walk-on that both sides will remember differently.
9A rope over the ledge, taut and creaking, and a man sawing at its anchor. He stops when he sees the party. The man on the rope’s end starts shouting too. Each swears the other is the thief and the map is in his pack — and one pack is on the rope-man’s back, going wherever he goes.
10The Sisters of the Scree. The framed encounter — written out in full in this Keeper: the read-aloud, the GM truth, the choice, outcomes, and scaling.

Roll it here: — or in DM Tools → Random Tables.

Framed: The Sisters of the Scree

Read aloud

The Weeping Stair is a long climb of switchbacks cut into wet gray rock, the only path over this shoulder of the mountain, and the guide-post at the bottom is furred with old ribbons and older wax plugs. High on the scarp, two shapes ride the wind without moving their wings. The singing starts before anyone sees them clearly. It isn’t loud. It’s the tune your mother hummed, or near enough, coming out of all that empty air, and every step of the Stair is a step toward it.

What’s really going on

Two harpies nest above the Stair. There were three sisters; a rockslide took one in the spring, and her chicks live. The survivors sing because song is how harpies feed a family — lured meat falls, or walks, to the nest ledge. They are not clever and not cruel; they are hungry, doubled. The old goatherds knew the arrangement — a carcass at the guide-post bought a season’s silence — but the goatherds are gone and nobody told the road.

The choice

Feed them, fight them, or cross under the song. The guide-post wax and ribbons are the previous generation’s answer, still legible to anyone who asks what they’re for.

What the party can do
  • The crossing is a 4-segment clock (preloaded in DM Tools). Each segment is one exposed stretch, one round long. Each round on the Stair, anyone who can hear the song makes the harpies’ DC 11 Wisdom save or spends that round walking toward the nest ledge instead of forward — which, on the Stair, means toward the edge.
  • Wax-plugged ears give advantage on the save, and take away every shouted warning and the sound of falling rock. Roped together, a charmed character can be held to the path — one hand free, half pace, the clock fills slower.
  • A night crossing meets no song (they roost), and trades it for DC 13 Strength (Athletics) on two of the four segments, in the dark, with the drop. Failure means a caught rope, a lost pack bouncing into the dark, and a segment lost — never a silent fall.
  • A mule’s weight of meat at the guide-post buys the party a silent crossing and costs the party a mule. This is the old price, and it still works.
Budget (four 3rd-levels)

As a straight fight, two harpies are 600 adjusted XP — medium on flat ground. The Stair is not flat ground. They dive, they sing, and they let the mountain do the damage.

Outcomes

Feed them and the road stays open behind you — the arrangement can be taught to the next village down, which is worth more than the mule. Kill them and the chicks starve loudly for a week within earshot of the pass, and travelers’ songs get safer and the nights get worse. Cross clean and the sisters remember the shape of you, without appetite. They’re patient.

What the party leaves with: the nest, if they climb for it or kill for it: 30 gp of woven-in glitter — buttons, buckles, a chain — and a signal-keeper’s mirror stamped with the beacon-line’s mark, which the scout from row 7 will very much want explained.

Scaling

Levels 1–2: one harpy; the clock does the work. Levels 4–5: three (the aunt from the far scarp), and the save comes at disadvantage on the two exposed segments. Levels 6+: the party can simply kill them — so make the question the chicks, and who carries four flightless, screaming reasons the pass is about to get worse. Party of 3: the rope only covers two; someone climbs unheld. Party of 6: two ropes, two exposed segments each.

The coast

Low tide has pulled the sea back off the Teeth, and there she is.
Low tide has pulled the sea back off the Teeth, and there she is.

The coast is a border, and borders have smugglers, taxmen, wreckers, and things that come up from the other side. Everything here runs on the tide’s schedule, not the party’s: the crossing that exists twice a day, the cave that stops being a cave, the wreck that’s reachable for exactly one hour. The sea’s law is older and simpler than anyone’s writ — what the sea takes is the sea’s — and half the trouble on any shore is somebody arguing the point.

What the tide leaves — d10
d10The encounter
1Two sahuagin stranded in a tide pool, spitting fury, helpless for six hours and lethal at flood. Kill them, ransom them back to the sea, or sit and watch the water rise on the conversation. Their kin remember either answer.
2A beached whale, alive, and the village already cutting. Flensing knives in it while it breathes, because winter is real. One hermit, shrieking from the rocks that killing it curses the whole shore. He might be right. He is definitely also hungry.
3The storm’s wreckage line, and two survivors. Each swears the other is the mutineer. Between them, half-buried, the strongbox that settles it — and opening it settles more than that, because the papers inside implicate both of them. And the owner’s mark on the box is somebody the party knows.
4A press-gang working the beach road. Four bandits and a big quiet one with a writ that’s real one county over, “recruiting” for a crew that’s short six hands. They’re polite right up until the party’s smallest member looks portable.
5Three giant crabs, working a body in the shallows. The body is armored. The armor is good. The crabs disagree about the order of operations, and the tide is bringing more of both.
6A lantern out on the rocks, swinging a pattern at dusk. Answer it in kind and a merrow surfaces at arm’s length with a net of drowned men’s goods — rings, blades, a captain’s glass — and prices that are never coin. It buys secrets. It sells the same.
7A rowboat crew burying kegs by moonlight, and now they’ve seen you seeing them. The first mate starts talking fast, because the captain’s standing rule about witnesses is a thing he’s done before and would rather not do again. The kegs are worth a lot. His hesitation is worth more.
8A cabin girl up a sea stack, gulls around her, refusing to come down. Her ship beached for repairs this morning. She says what came out of the hold is wearing the bosun’s coat now, and doing the voice, and the crew won’t hear a word against the bosun. The girl counts better than she explains: they beached with nine. There are nine on the sand. The bosun makes ten.
9Fisherfolk hauling a net that hauls back. They’ll pay for strong arms, no questions asked. In the net: a giant octopus, the season’s whole catch, and somebody’s drowned husband, and the octopus lets go of exactly none of it for free.
10The Wreck of the Gull’s Wager. The framed encounter — written out in full in this Keeper: the read-aloud, the GM truth, the choice, outcomes, and scaling.

Roll it here: — or in DM Tools → Random Tables.

Framed: The Wreck of the Gull’s Wager

Read aloud

Low tide has pulled the sea back off the Teeth, and there she is: a coaster on her side far out across the wet sand, hull cracked like a mussel shell, cargo netting still full. The tide turned minutes ago. Out to the south, a longboat is already rowing, oars pulling hard, a red-bearded man at the tiller watching the party the way a foreman watches a rival crew arrive at the same seam of coal. And along the wreck’s waterline, something the length of the longboat slides through the flooded half of the hull without ever quite showing all of itself.

What’s really going on

The Gull’s Wager struck the Teeth in last night’s storm. Redland Hesk beached his crew’s boats a bay south and means to strip her before the excise cutter comes out at the next high water; he has three bandits at the oars and a firm policy that salvage stories travel better with no second crew in them. The ship’s boy, the eighth soul aboard, is alive in the rigging, and knows where the strongbox is.

What Hesk doesn’t know: a merrow got there at first light. It isn’t after the silk. It’s collecting the crew — the drowned belong below, by a law older than excise — and it has four of the seven. The other three are sand-buried in the surf gap between the wreck and the shore. Offer it the three buried crewmen and it goes indifferent. Offer it Hesk’s opinion on the subject and you’ve bought the fight of the day.

The choice

Race, deal, or hold. Split the salvage with Hesk’s crew (he’d honestly rather add hands than bodies, whatever his policy says), hold the wreck against him, or work out what the merrow actually wants and give it — at which point the wreck’s worst problem starts solving its other one.

What the party can do
  • The tide is a 6-segment clock (preloaded in DM Tools). It fills one segment per round of fighting or per ten minutes of work, whichever the scene is doing. At three segments the surf gap is waist-deep and the sand-buried dead are floating. At six, the Teeth are sea again and everyone still aboard is swimming.
  • The strongbox costs two segments of work and a DC 13 Strength (Athletics) check to pry the mate’s cabin open; failure costs a third segment, not the box. Bring the ship’s boy down first and he points straight to the right cabin — the whole job costs one segment.
  • Spotting what the merrow is actually doing — taking bodies, ignoring bales — is a DC 15 Wisdom (Perception) check , or automatic the moment anyone watches it for a full round.
  • Hesk parleys at half strength, or the moment the merrow takes one of his oarsmen. His opening offer is a third. His honest ceiling is half.
Budget (four 3rd-levels)

Hesk (bandit captain, 450 XP) + three bandits (25 each) = 525 raw ×2 = 1,050 adjusted — hard. The merrow is not on the total: it is a third side, and it spends its harpoon on whichever crew is winning. Say that out loud to yourself before round one; it makes the fight.

Outcomes

Split with Hesk and the party gains a smuggler’s respect and the excise cutter’s attention, in that order. Hold the wreck and they’ve made a patient coastal enemy with a long memory for faces. Feed the sea its due and the merrow leaves the living alone — and surfaces once, later this campaign, to repay it; the sea keeps accounts too.

What the party leaves with: their share — up to 200 gp in silk and brandy at a fair fence, the mate’s strongbox (60 gp, the manifest, and the excise seal of a port official who was insuring cargo he was also selling — a hook with teeth), and the ship’s boy, who needs a berth and knows every harbor rumor on this coast.

Scaling

Levels 1–2: two oarsmen, no merrow — the tide and Hesk are plenty. Levels 4–5: five oarsmen and Hesk’s mate (a second captain). Levels 6+: the excise cutter arrives at segment four, and now there are four sides and one strongbox. Party of 3: Hesk offers the deal first, fights only if robbed. Party of 6: two merrow; the drowned crew was owed double.

Cast & stat lines

Every framed roster is pre-loaded in DM Tools → Combat. SRD statblocks, compressed to what you use at the table.

Maren of the Cut (druid)

Druid · CR 2 (450 XP) · AC 11 (16 with barkskin) · HP 27 · Speed 30 ft

Spells that matter: entangle (DC 12, 20-ft square, restrained), thunderwave (DC 12, 2d8), barkskin, cure wounds. Opens with entangle; yields below half HP. ·

Her wolves (×2): AC 13 · HP 11 · bite +4 (2d4+2, DC 11 STR or prone) · pack tactics. They break when she yields.

Old Hob (ghast)

Ghast · CR 2 (450 XP) · AC 13 · HP 36 · Speed 30 ft · stench (DC 10 CON, 10 ft)

Claws. · and DC 10 CON or paralyzed 1 minute (repeat save each turn). Bite +3, 2d8+3.

The passengers (ghouls ×2): AC 12 · HP 22 · claws +4 (2d4+2, DC 10 CON or paralyzed; elves immune). They board at the ends of rounds two and three.

The Sisters of the Scree (harpies ×2)

Harpy · CR 1 (200 XP each) · AC 11 · HP 38 · Speed 20 ft, fly 40 ft

Luring Song. DC 11 WIS save or charmed: move toward the harpy by the safest route; repeat the save on damage. On the Stair, “toward” means the edge.

Multiattack. Club (2d4+1) and claws +3 (2d4+1). They dive, sing, and let the mountain do the damage.

Redland Hesk (bandit captain)

Bandit captain · CR 2 (450 XP) · AC 15 · HP 65 · Speed 30 ft

Multiattack. Two scimitar (1d6+3) and dagger +5 (1d4+3). Parry (reaction): +2 AC vs one melee attack.

His oarsmen (bandits ×3): AC 12 · HP 11 · scimitar +3 (1d6+1). Parley at half strength, or the moment the merrow takes one of them.

The merrow of the Teeth

Merrow · CR 2 (450 XP) · AC 13 · HP 45 · Speed 10 ft, swim 40 ft

Multiattack. Bite (1d8+4) and harpoon +6 (2d6+4; a Large or smaller target pulled 20 ft on a failed DC 14 STR contest).

A third side, not a monster wave: it spends its harpoon on whichever crew is winning, and goes indifferent the moment the drowned are given back.

Running it in other systems

Nothing here is welded to a stat block. The tables are system-free as written; for the framed encounters, swap each named creature for your system’s equivalent at the party’s tier (a wilderness guardian, a mid-tier undead, two flying skirmishers, a human gang boss with muscle), keep the DCs as “easy / moderate / hard” in your system’s terms, and run the clocks exactly as they are — a 4-segment climb and a 6-segment tide work at any table that can count.

If this Keeper earns a spot at your table

This is what an Adventure Keeper is: the adventure and the tools in one offline file, dice and trackers and clocks included, yours forever. This one’s free, and it stays free.

There’s a complete free one-shot Keeper too — The Keeper of Halcyon Light — waiting at longislanddungeonmaster.com/keepers. Every other Wednesday, paid subscribers to The Bi-Weekly One-Shot get a full new adventure built exactly like this — villain first, choices that matter, the whole kit — delivered as a Run Deck and a print PDF they keep. And if you’d rather own one outright, the flagship one-shots live on the LIDM storefront on itch.io.

Roll well.

Long Island Dungeon Master

Compatible with fifth edition. Portions of this work are derived from the System Reference Document 5.1, © Wizards of the Coast LLC, available under the Creative Commons Attribution 4.0 International License (CC-BY-4.0). Where the Road Ends, Maren of the Cut, Old Hob, the Sisters of the Scree, Redland Hesk, the Gull’s Wager, the Weeping Stair, and the Teeth are original content © Long Island Dungeon Master.

DM cheat sheet

Auto-built from every data-dc, data-hp, stat block, preset clock and pre-loaded combatant in this file. Prints on its own sheet.