The Highwayman’s Camp is a small but fortified outpost nestled at the crossroads of a winding river and several well-traveled roads deep within the woods. The camp is a strategic location, offering easy access to the surrounding regions, making it an ideal rest stop for those who need to pass through undetected—or for those with less noble intentions.
At the heart of the camp, two modest wooden structures stand prominently: the Main Storehouse, which holds provisions and supplies, and the Highwayman’s Lodge, a simple but sturdy building where the band’s leader resides and holds meetings. Both are built to withstand the elements and any potential skirmishes, with reinforced walls and simple defensive features.
Closer to the river, a cluster of weathered tents houses the rest of the band. These temporary structures serve as living quarters for the highwaymen and their companions, offering little in the way of luxury but plenty of shelter for those accustomed to the harsh life of outlaw living. The scent of campfires and the murmur of voices can often be heard from this area, especially as the camp winds down for the night.
Despite the lack of formal sentries, the camp is well-defended. Its position at the crossroads allows for easy surveillance of the surrounding area, and the natural defenses offered by the dense woods and fast-moving river make it difficult for enemies to approach unnoticed. The highwaymen rely on the environment to keep them safe, setting up traps and watchful eyes along the approaches.
The camp’s self-sufficiency is bolstered by a small but well-maintained garden, where herbs, vegetables, and small fruits grow in abundance. The band trades or barters the goods they harvest, supplementing their diet with what they can scavenge or “liberate” from travelers passing through the nearby roads. The nearby river also provides fishing opportunities, ensuring the camp remains well-fed. However, the true wealth of the camp is built on its more unsavory activities: robbing and ambushing the occasional unfortunate traveler, whether by road or by river, to support their lifestyle.
Though small in size, the Highwayman’s Camp is a hub of activity, with a constant ebb and flow of people coming and going—some by choice, others out of necessity. For the highwaymen, it is both home and base of operations, from which they can quickly disperse or regroup depending on the situation.
Encounters at the Highwayman’s Camp
The Highwayman’s Camp is a dynamic and unpredictable location, serving as both a place of rest for some and a dangerous hideout for others. Whether the party stumbles upon it by chance, is sent there on a mission, or finds themselves caught up in the camp’s activities, the band of outlaws that reside here will offer both opportunities and challenges. The encounters detailed below provide a variety of ways the party can interact with the camp and its inhabitants, depending on the situation or the motivations behind their visit.
Each encounter is designed to be flexible, allowing you to incorporate them into your campaign in a way that best fits your storyline. Whether you wish to create a tense, stealth-driven infiltration or a more casual encounter based on trade and negotiation, these scenarios can be adapted to suit the tone of your game.
When incorporating these encounters, consider the following:
- The Party’s Motivation: What brings the party to the camp? Are they there to recover something, trade supplies, or simply pass through? The party’s goals will influence how they interact with the Highwaymen and what challenges they face.
- The Mood of the Camp: The Highwaymen might be on high alert, celebrating a successful raid, or preparing for a major operation. This mood can shift the tone of the encounter, affecting everything from the camp’s level of hospitality to the aggression they show toward outsiders.
- Player Choices: The Highwaymen are not just enemies to be fought—they are individuals with their own goals, alliances, and personalities. Encourage your players to think creatively in how they approach the camp, whether they choose to negotiate, sneak, or fight their way through.
Friendly Trading Post or Restocking Point
The camp is a bustling, makeshift trading post where travelers can rest and resupply. The Highwaymen run this place as a neutral spot, offering goods for trade or bartering in exchange for supplies, information, or services. However, the exchange rate might be skewed—perhaps the band asks for a bit more than usual, or there are rumors that the goods available aren’t always as advertised.
While the camp seems like a peaceful stop, there’s always the lingering sense that things are never entirely above board. Some of the traders or travelers might have been taken advantage of in the past. The party could overhear whispers about shady dealings or missing items.
The Highwaymen Are Bandits
The Highwaymen are notorious bandits who ambush travelers, taking what they can. As the party enters the camp, it becomes clear that the band expects a “donation” to use the roads. Perhaps the party has something of value that the Highwaymen have taken an interest in, or they simply decide to extort them for a toll.
The bandits might allow the party to leave with their lives if they pay a hefty ransom or offer something of value. Alternatively, the leader might want to test the party’s strength, setting up an ambush to see if they are worth robbing, or perhaps they want to turn the party into pawns for a bigger scheme.
If the party tries to negotiate their way out, the Highwaymen might play the “honor among thieves” card and offer a trade, asking the party to choose between valuable goods or performing a task in exchange for their lives.
The Party Needs to Recover Something Stolen
The Highwaymen recently raided a nearby caravan or town, taking something of great importance—perhaps an artifact, a letter, or a family heirloom that the party needs to recover. The party must track down the item, which is likely hidden within the camp. They will need to either talk to band members, search for clues, or even use stealth to avoid getting caught while they search.
If the party decides to be stealthy, they could encounter traps or guards they need to avoid, leading to tense moments as they sneak through the camp. Or, if they confront the band, the Highwaymen could offer the item back—but only in exchange for a favor.
Possible Twist: The item is hidden in plain sight, and the Highwaymen are aware of its importance, setting up a bait-and-switch to lure the party into a trap. Alternatively, the party could discover that someone inside the camp isn’t exactly who they seem—perhaps a spy or informant working for a rival group.
A Happenstance Encounter
The party happens upon the camp by chance while traveling, and what they think will be a simple stop turns into a more complicated situation. Perhaps a member of the party has a past with the Highwaymen, or a member of the band recognizes the party for some reason. This encounter could start with a sense of ease—resting for a few hours or gathering information—but quickly turn into something more personal, especially if the Highwaymen have their eyes on the party for a specific reason.
The mood of the camp could shift depending on how the party reacts. If the party is bold, they may be greeted warmly or invited to join in a feast. If they act with suspicion or seem too much like “outsiders,” the Highwaymen might close ranks and prepare for a confrontation.
Possible Twist: The Highwaymen might not recognize the party as heroes or adventurers, and instead see them as prime targets for a robbery or extortion. Alternatively, a former ally or acquaintance might be found among the band, offering a chance for some inside information or a negotiation.
The Party Needs Stealth to Avoid Detection
The party arrives at the camp under the cover of night, needing to pass through without being noticed. Maybe they’re on a mission to spy on the Highwaymen or recover something from the camp without alerting the band to their presence. This encounter tests the party’s stealth, as they will need to avoid sentries, patrols, and possibly even traps set up around the camp.
The layout of the camp itself could create challenges—narrow paths, hidden watchposts, and thick underbrush near the river could all provide opportunities for the party to hide, but also risk being ambushed by alert Highwaymen.
Possible Twist: If the party is caught sneaking around, the Highwaymen might decide to use them as hostages, forcing the party to fight their way out or negotiate for their release. Alternatively, the band might respect the party’s stealth and try to recruit them for a future raid, offering a deal.
The Consequences of Walking Into the Camp
The party walks right into the open gates of the Highwayman’s camp, fully aware that they are entering a dangerous place. The Highwaymen could react in various ways depending on the party’s attitude. Are they acting aggressively or as if they own the place? Are they going to try and talk their way through, or simply fight their way out? The leader may approach them directly, offering a challenge or a deal.
The Highwaymen will test the party’s mettle, perhaps leading to a negotiation or a confrontation. If the party tries to intimidate the band, it could result in a bloody skirmish. If they try to talk, they may find themselves locked into a dangerous game of deception and manipulation.
The Highwaymen could take a liking to the party, offering them a spot in the group—or they could see the adventurers as a threat, quickly sizing them up for an ambush or a trial by combat. Alternatively, the leader might have a personal vendetta, and the encounter could escalate based on past encounters or old wounds.
The Highwaymen
The Highwaymen are a motley group of outlaws, each with their own story but united by a common cause: survival and profit. Based at their camp near a crossroads along the river, the band operates as both a trading post for those brave enough to barter and a merciless group of bandits preying on the unwary. Though their actions lean toward the criminal, there’s more to them than just violence and thievery. The Highwaymen have developed a complex society within their camp, where each member plays a critical role, and relationships are shaped by loyalty, respect, and necessity.
Each of these individuals plays a key role in the Highwaymen’s operation, and their interactions with the party can vary based on the group’s goals, the party’s actions, and the situation at hand. Whether the party is looking to negotiate, gather information, or simply survive a tense standoff, these NPCs offer a wealth of opportunities for alliances, conflict, and unexpected twists.
Rogan “The Blade” Wilder – Leader
Rogan is a charismatic and calculating leader, known for his quick wit and even quicker sword. He stands tall with a commanding presence, always dressed in well-worn but functional armor. His sharp eyes miss nothing, and his reputation as both a ruthless bandit and a clever negotiator precedes him. Although his methods are often violent, he values loyalty above all else and respects those who can hold their own in a fight or offer something valuable to his cause. Rogan is not above making deals, but beware—he’s a master manipulator, always playing several games at once.
Kaela Thorne – Quartermaster
Kaela is a no-nonsense woman who runs the day-to-day operations of the camp. With her sharp mind and even sharper tongue, she ensures the band has everything they need—whether it’s food, weapons, or the occasional “new recruit” from passing travelers. She’s the one who organizes the bartering and makes sure that no one in the camp is going without. Kaela keeps a level head, even in tense situations, and tends to be one of the more reasonable members of the group. But don’t mistake her calm demeanor for weakness—she can hold her own in a fight and is fiercely protective of the camp’s well-being.
Finnian Greenleaf
Finn is an elusive and skilled tracker, the eyes and ears of the camp. He has a quiet and reserved demeanor but is always alert, watching from the shadows. His clothing is patchwork, designed for blending into the woods, and his face is always partially covered by a scarf or hood. Finn is a master of stealth and has an uncanny ability to track anyone, even through the densest of forests. Though he’s not the most sociable, he’s well-respected by the band for his skills and is often the first one sent out on any scouting or ambush missions. He doesn’t speak much, but his actions speak louder than words.
Alina “Silver Tongue” Varo
Alina is a sharp-tongued, silver-eyed woman who is always in the know about what’s happening outside the camp. She has connections in every town and city and can be the source of valuable information for Rogan, whether it’s about the movements of a caravan or rumors of a lucrative target. Alina is charming, witty, and knows how to talk her way into or out of nearly any situation. She keeps her cards close to her chest, and while she’s a trusted ally of Rogan’s, her true loyalties may be more flexible than she lets on. Alina could be a valuable source of information for the party, though they’ll have to decide if they trust her.
Jorri Bellwood
Jorri is a quiet, gentle soul who serves as the camp’s medic. Though he’s a member of the band, he often seems out of place, preferring to spend his time studying herbs or caring for the wounded in his small tent. He’s known for his quick hands and calm demeanor, even in the midst of chaos. While he’s not involved in the banditry, Jorri’s skills make him an invaluable member of the group, and Rogan keeps him around for his medical expertise. Jorri has a kind heart but is often conflicted about the violence of the bandit life, and he might be swayed by a party who offers help or a way out of the lifestyle.