D&D 5E (2024) The Black Road - Help me flesh out an Adventure idea.

Oh - one more thing - is there going to be an over-arching storyline? And also, relatedly, how will you handle the "rising power" of the PCs? What was challenging for 1st level guards won't be at all challenging at 5th level, much less 10th level.

I think not a big plot, exactly, other than the stated "Get the Caravan to Phlan". Subplots and pickup threads aplenty, though.

I've never had trouble with the rising power of the PCs, other than that I generally prefer more mundane themes than gonzo supers. But I can balance encounters well, and I'm happy to use homebrew and 3rd party monsters, including things like using the Swarm rules to model Units of 8-12 combatants as higher-CR "monsters", rather than hordes. For example, I have run battles with 60-100 soldiers modelled as only 5-8 "creatures" (when it comes to bases and statblocks). For example, a single huge creature that models a Unit of a dozen Pikemen. I could conceivably do a Bandit Raid that way, just off the top of my head. Does that make sense?
 

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Tyranny of Dragons has a section where characters are on a month-long caravan trek from Baldur's Gate to Waterdeep. It has several drop-in encounters that would be worth raiding, I believe.

Below is a couple of encounters I drafted up for a Ravenloft halloween one-shot a few years back. With a few place-name changes, I would think any of these might make for interesting encounters along the road.
ENCOUNTER 1 - Raiders

"You have just traveled beyond the burned out ruins of the city's last watchtower and turned onto the overgrown trail known as the Watcher's Road. Years of disuse has seen it almost reclaimed by the ancient Vigilia forest, whose black woods climb into the sky to each side. There is a screech as a hawk lifts off from one of the creaking nearby tree, and not a moment later the deep bellow of a hunting horn sounds from the thick underbrush. In a flash, the way ahead is blocked by six riders - their features hidden behind the animal pelts they wear. Each rides a lean, yet powerful wolf. Ahead of them steps a tall, thick man nearly seven feet tall and dressed like the others, but wearing a helm adorned with antlers - whose bloody felt still drips from its tines. To his right and left stand emanciated and hairy men, their faces impossibly scrunched into savage, animalistic snarls. They raise their weapons, and with a low growl from the tall man, the whole company moves towards you. 'Kill the guards,' he commands, 'take the others alive!'

6 Bandits riding trained wolves, led by a bandit captain and his two shifters. They attempt to draw the PCs away from their charges so they can kidnap the workers and take them back to their lair. There are 10 slaves at the bandit's lair, under the watchful eye of an ex-captain of the guard.

ENCOUNTER 2 - Abandoned Wagon

"The muddy road opens into a rocky glade. The trees themselves seem to pull back to reveal a colorful, covered wooden wagon to one side of the road - easily identified as a Visanti's vardo. One of it's wheels has been visibly hacked to pieces and the colorful banners that adorned it now hang tattered and fluttering in the wind. A silent mare still stands tied to the front of the wagon, but its driver is nowhere to be seen. As the rear door clatters against the wagon in the stiff wind, the startled horse shivers a moment, but does not otherwise move."

An abandoned vardo on the side of the road. One dead horse lies nearby, half-gnawed to bone. The other horse is still tethered to the wagon and is a zombie. A body lies face down nearby, its face is missing (not torn off or mutilated, simply blank). The vardo has been ransacked; if the inside is investigated, there is a locked chest inside with a potion of healing, a bandana of luck and the knight card from a tarokka deck (turns into a knight if thrown down on the ground). Struck into the center of the vardo is a blood-stained silver long sword. The vardo is covered and provides better protection from attack, but is much heavier - it must either be drawn by the zombie horse or a team of 5 men of STR 12 or better.

If the party investigates the area, each PC makes a Perception check. The PC that rolls lowest (and below 15) is ambushed by a Strahd Zombie - the corpse of one of the Visanti that owned the wagon. The rest of the group is attacked by 3 boneless and a Deathlock. One round later, a line of zombies appears at the forest's edge, and 6 Strahd Zombies stride forward to join the fray; the rest not venture out into the light. After three rounds, a hunting horn sounds and the remainder turn and shamble back into the woods.

ENCOUNTER 3 - The Homestead

"Ahead in the distance, you can just make out the Tripoint, where the Watcher's Road bisects the Hunter's Way. But just ahead the woods have been cut back, the jagged stumps testimony to their sad fate. Amid the clump of hewn trees stands the half-collapsed, half-burned ruin of a homestead. Only the chimney and a few charred upright timbers remains amid the swept dirt-packed foundation, and a faint wisp of smoke escaping the stacked stones. Somewhere nearby, you hear the faint cry of a baby and the enticing aroma of bacon wafts into your nostrils."

The party nears a burned out homestead. Only a few wooden beams and the stone chimney remains. There is a strong smell of bacon in the air, and a thin wisp of smoke comes from the chimney. As the party nears, they hear faint, muffled cries of a baby or child. Hidden behind the chimney is the wife. In the nearby woods is the father, a survivor armed with a wood axe. Hidden under the floorboards is the cellar, where the family stays and the couple's young child stays. There are also hand-crafted crates stored here to gather the harvest hidden nearby.

A passive Perception DC 15 (or searching) reveals an odd blue shade to the nearby green underbrush. Examination reveals it is a bean farm (String beans, lima beans, peas) with enough that it would take a work force of 20 pickers 4 hours to gather.

Characters have to decide to leave the family behind, take them with them as workers, and whether or not to take the child (an extra mouth too young to work).

After the party deals with the family, a pack of 3 starving dire wolves , led by a dire wolf attack.

If the party decides to pick the harvest, 2 skeletons, 2 zombies covertly attempt to attack the pickers, while a swarm of zombie limbs and a Zombie plague spreader attack the PCs. On the 3rd round, a diseased Hill Giant enters the fray, attempting to make a meal of anyone that gets too close.

ENCOUNTER 4 - The Crossing

"Your travels along the Hunting Way have brought you to the Dragon's Bridge, the stone bridge that is the only way over the dark, swift current of the Drogach River. To your dismay, the stone bridge has fallen, its powerful arch collapsed by what looks to have been an action rearguard action to deny the enemy its use. But hope remains, for a rough trail leads down beside the huge flagstones to the river's edge. Across the thirty-foot span the trail picks up and rejoins the road. But slightly to the south, along the line of the river's current lay the teeth of the bridge's fallen rocks and a mire where broken wagons and bones alike like silent and staring on the far shore."

The party arrives at the bridge an hour away from the settlement. The stone bridge is out, with the supports still in place, and a littering of large rocks nearby (looks like the bridge was deliberately collapses by a rear-guard action). Well-worn wagon tracks lead down the slope to the right of the bridge, and a muddy expanse on the far side, littered with broken wagon parts shows evidence that crossing attempts (not all of which were successful) occur here. The river is 30 feet wide, swift and about 10 feet deep (though wine-dark)

The party must secure the wagon to float it across, deciding who will be aboard and who will swim/wade across. It takes three successful DC 15 Strength checks to get the wagon across. Three failures means the wagon is swept against the rocks and crushed. Each individual failure means the wagon drifts downstream, off-course and closer to the rocks.

Swimmers must make two DC 12 Athletics check to swim/wade across. One failure indicates the swimmer is swept toward the ghoul's pit. Two failures indicate that the swimmer is swept to the ghoul pit and dashed against rocks, taking 3d6 damage.

Hidden amid the wreckage on the far side is a pack of 4 ghouls and their pet Catoblepas (arrives to the fight a round after the zombies), waiting to ambush those who make it across. There are also 4 Strahd zombies on the near side if the party arrives at night, who attack as the party investigates the area or as they start their crossing.

Pit Treasure: [200 cp, 9,000 sp, 2,100 gp, 120 pp, 13 50 gp gems] in a bag of holding, 10 arrows +1 scattered about, and one of the ghouls wears a robe of useful items.

Also, as an aside, Gentle Repose or a variant of it might be an excellent way to preserve perishable goods being carried.
 

Tyranny of Dragons has a section where characters are on a month-long caravan trek from Baldur's Gate to Waterdeep. It has several drop-in encounters that would be worth raiding, I believe.

Below is a couple of encounters I drafted up for a Ravenloft halloween one-shot a few years back. With a few place-name changes, I would think any of these might make for interesting encounters along the road.
ENCOUNTER 1 - Raiders

"You have just traveled beyond the burned out ruins of the city's last watchtower and turned onto the overgrown trail known as the Watcher's Road. Years of disuse has seen it almost reclaimed by the ancient Vigilia forest, whose black woods climb into the sky to each side. There is a screech as a hawk lifts off from one of the creaking nearby tree, and not a moment later the deep bellow of a hunting horn sounds from the thick underbrush. In a flash, the way ahead is blocked by six riders - their features hidden behind the animal pelts they wear. Each rides a lean, yet powerful wolf. Ahead of them steps a tall, thick man nearly seven feet tall and dressed like the others, but wearing a helm adorned with antlers - whose bloody felt still drips from its tines. To his right and left stand emanciated and hairy men, their faces impossibly scrunched into savage, animalistic snarls. They raise their weapons, and with a low growl from the tall man, the whole company moves towards you. 'Kill the guards,' he commands, 'take the others alive!'

6 Bandits riding trained wolves, led by a bandit captain and his two shifters. They attempt to draw the PCs away from their charges so they can kidnap the workers and take them back to their lair. There are 10 slaves at the bandit's lair, under the watchful eye of an ex-captain of the guard.

ENCOUNTER 2 - Abandoned Wagon

"The muddy road opens into a rocky glade. The trees themselves seem to pull back to reveal a colorful, covered wooden wagon to one side of the road - easily identified as a Visanti's vardo. One of it's wheels has been visibly hacked to pieces and the colorful banners that adorned it now hang tattered and fluttering in the wind. A silent mare still stands tied to the front of the wagon, but its driver is nowhere to be seen. As the rear door clatters against the wagon in the stiff wind, the startled horse shivers a moment, but does not otherwise move."

An abandoned vardo on the side of the road. One dead horse lies nearby, half-gnawed to bone. The other horse is still tethered to the wagon and is a zombie. A body lies face down nearby, its face is missing (not torn off or mutilated, simply blank). The vardo has been ransacked; if the inside is investigated, there is a locked chest inside with a potion of healing, a bandana of luck and the knight card from a tarokka deck (turns into a knight if thrown down on the ground). Struck into the center of the vardo is a blood-stained silver long sword. The vardo is covered and provides better protection from attack, but is much heavier - it must either be drawn by the zombie horse or a team of 5 men of STR 12 or better.

If the party investigates the area, each PC makes a Perception check. The PC that rolls lowest (and below 15) is ambushed by a Strahd Zombie - the corpse of one of the Visanti that owned the wagon. The rest of the group is attacked by 3 boneless and a Deathlock. One round later, a line of zombies appears at the forest's edge, and 6 Strahd Zombies stride forward to join the fray; the rest not venture out into the light. After three rounds, a hunting horn sounds and the remainder turn and shamble back into the woods.

ENCOUNTER 3 - The Homestead

"Ahead in the distance, you can just make out the Tripoint, where the Watcher's Road bisects the Hunter's Way. But just ahead the woods have been cut back, the jagged stumps testimony to their sad fate. Amid the clump of hewn trees stands the half-collapsed, half-burned ruin of a homestead. Only the chimney and a few charred upright timbers remains amid the swept dirt-packed foundation, and a faint wisp of smoke escaping the stacked stones. Somewhere nearby, you hear the faint cry of a baby and the enticing aroma of bacon wafts into your nostrils."

The party nears a burned out homestead. Only a few wooden beams and the stone chimney remains. There is a strong smell of bacon in the air, and a thin wisp of smoke comes from the chimney. As the party nears, they hear faint, muffled cries of a baby or child. Hidden behind the chimney is the wife. In the nearby woods is the father, a survivor armed with a wood axe. Hidden under the floorboards is the cellar, where the family stays and the couple's young child stays. There are also hand-crafted crates stored here to gather the harvest hidden nearby.

A passive Perception DC 15 (or searching) reveals an odd blue shade to the nearby green underbrush. Examination reveals it is a bean farm (String beans, lima beans, peas) with enough that it would take a work force of 20 pickers 4 hours to gather.

Characters have to decide to leave the family behind, take them with them as workers, and whether or not to take the child (an extra mouth too young to work).

After the party deals with the family, a pack of 3 starving dire wolves , led by a dire wolf attack.

If the party decides to pick the harvest, 2 skeletons, 2 zombies covertly attempt to attack the pickers, while a swarm of zombie limbs and a Zombie plague spreader attack the PCs. On the 3rd round, a diseased Hill Giant enters the fray, attempting to make a meal of anyone that gets too close.

ENCOUNTER 4 - The Crossing

"Your travels along the Hunting Way have brought you to the Dragon's Bridge, the stone bridge that is the only way over the dark, swift current of the Drogach River. To your dismay, the stone bridge has fallen, its powerful arch collapsed by what looks to have been an action rearguard action to deny the enemy its use. But hope remains, for a rough trail leads down beside the huge flagstones to the river's edge. Across the thirty-foot span the trail picks up and rejoins the road. But slightly to the south, along the line of the river's current lay the teeth of the bridge's fallen rocks and a mire where broken wagons and bones alike like silent and staring on the far shore."

The party arrives at the bridge an hour away from the settlement. The stone bridge is out, with the supports still in place, and a littering of large rocks nearby (looks like the bridge was deliberately collapses by a rear-guard action). Well-worn wagon tracks lead down the slope to the right of the bridge, and a muddy expanse on the far side, littered with broken wagon parts shows evidence that crossing attempts (not all of which were successful) occur here. The river is 30 feet wide, swift and about 10 feet deep (though wine-dark)

The party must secure the wagon to float it across, deciding who will be aboard and who will swim/wade across. It takes three successful DC 15 Strength checks to get the wagon across. Three failures means the wagon is swept against the rocks and crushed. Each individual failure means the wagon drifts downstream, off-course and closer to the rocks.

Swimmers must make two DC 12 Athletics check to swim/wade across. One failure indicates the swimmer is swept toward the ghoul's pit. Two failures indicate that the swimmer is swept to the ghoul pit and dashed against rocks, taking 3d6 damage.

Hidden amid the wreckage on the far side is a pack of 4 ghouls and their pet Catoblepas (arrives to the fight a round after the zombies), waiting to ambush those who make it across. There are also 4 Strahd zombies on the near side if the party arrives at night, who attack as the party investigates the area or as they start their crossing.

Pit Treasure: [200 cp, 9,000 sp, 2,100 gp, 120 pp, 13 50 gp gems] in a bag of holding, 10 arrows +1 scattered about, and one of the ghouls wears a robe of useful items.

Also, as an aside, Gentle Repose or a variant of it might be an excellent way to preserve perishable goods being carried.
I recently played through that sequence in Tyranny of Dragons, and it was pretty fun. Good faction play, worth reviewing I think.
 

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