A traveling caravan of traders has much to fear in their journeys as they plow a course from settlement to settlement. Out in the wilderness, roving bands of raiders prey on the weak, the foolhardy, and the naive. These brutal parties of opportunistic marauders stalk their quarry and launch surprise attacks that use the landscape to their advantage. Some raiding parties travel on steeds, riding animals of all varieties. Druidic peoples and their allies burst forth from the forests armed with bow and spear and mounted on slavering wolves. From a distance, hunters assail their targets with arrows and blasts of arcane energies. Each company of raiders uses different methods, which they have refined over many escapades. Their motivations also differ: some attack to protect their traditional lands while others do so for money. Some raiders may even just do it for glory and pride.
Downtime: This is a Stick Up
Caravans and traders make for worthwhile sport and even worthier targets, as do scouts from rival tribes. As a downtime activity (/dt-nightraider), you can set out to ambush travelers and locals on the roads. Choose and roll a d4, d6, d8, or d10. A roll of 1 and a roll that is greater than the character’s Wisdom modifier + proficiency bonus is considered a failure. The company gains 10 gp × the sum of the successful rolls. If the total number of failures is greater than the Wisdom modifier + proficiency bonus among all the company’s members, the raid results in a conflict with a well-armed force that leads to the incarceration of the raider for a period of days equal to the number of failures.
Company Accomplishments
Your company’s prestige increases whenever you carve out your hunting territory and prove your ability through acts such as the following:
- Hijacking a caravan, or boat
- Destroying a rival tribe or company of raiders
- Breaking someone out of prison
- Stealing an item worth at least 1,000 gp
- Capturing and selling 1,000 gp worth of livestock
Prerequisites
Any character can belong to a Night Raiders company, but it must include at least one character proficient in Survival.

Tier 1 : Cattle Rustlers
At this tier, your company is a small number of armed warriors who make a living raiding farms and small holdings, along with any small group of traveling merchants. At this tier, your marks are usually farmers and caravans with herds or goods with a total worth of no more than 100 gp. You might operate as a small party of some larger group of bandits or outriders for a tribe.
Benefits
Hideout. You maintain a small camp somewhere in the scrubland or in a cave in the shadow of the mountains. Here you tend to whatever steeds and animals you have captured. You have tents for sleeping and a place where you stash your ill-gotten gains.
Martial Hand Signals. You can learn martial hand signals, which allows you and other members of your company to communicate silently, thereby allowing you to plan attacks without revealing your position via speech.
Tier 2 : Highway Bandits
At this tier, your company is a small number of armed warriors who make a living raiding farms and small holdings, along with any small group of traveling merchants. You might operate as a small party of some larger group of bandits or outriders for a tribe.
Benefits
Bandits. Novices and new recruits seek out your group to learn your ways and make a life for themselves. You gain 1d4 hirelings with a challenge rating of 1/4 or lower.
Improved Steeds. Your company has invested in its steeds and mounts, improving both their quality and their tack. While you are riding your steed, attack rolls targeting your mount are made with disadvantage.
Loyal Informants. Your network of contacts throughout the lands is such that you receive tips on valuable cargo being transported by caravans and on boats. You now have leads on targets carrying more of valuables or the movement of herds of an equivalent value. Your awareness of the movements of the groups allows you to plan better ambushes. The value of successes when performing a Stick Up is increased to 20 gp per success.
Tier 3 : Feared Raiders
Your band of raiders is now feared for many leagues around and spoken about in hushed tones in taverns and towns. Other bandits fear you and stay out of your territory, and tribal leaders come to you when they need extra muscle.
Benefits
Additional Camps. Your company contains no fools and therefore maintains 1 extra campsite per 3 members, in a different region than any other camp, where supplies are stashed in case you need to flee your regular camp.
Bandit Kings. Your company gains 2d8 hirelings with a challenge rating of 1/2 or lower. Half these new recruits have mounts with a challenge rating of 1/4 or lower.
Battle Steeds. Your steeds and mounts have been trained to deal lethal attacks with their hooves, claws, and tusks. As a bonus action, you can direct your mount to make one attack with one of its weapons.
Tier 4 : Lords of the Night
By the time your company has reached this tier, it has become renowned among raiders, feared by travelers and merchants, and wanted by the law across many of the surrounding areas. Your influence and notoriety are such that no caravan or merchant passes through your territory without employing guards and mercenaries. Lords and ladies curse your name and your impact on their citizens.
Benefits
Hardened Killers. Your company consists of trained killers. The number of hirelings you can have increases by 2d4, and your hirelings can have a challenge rating of 1 or lower. These new recruits ride on mounts with a challenge rating of 1/2 or lower.
Tithes. You claim a tithe of 200 gp a month from groups of raiders engaging in smaller actions.