I have been playing role-playing games since 1986 and most of that time has been as a Dungeons Master. Throughout my life, role-playing games have consistently been one of my favorite hobbies. I like to run a sandbox style campaign, developing my campaigns as a loose idea that forms to meet the player characters. Often this means gaming sessions do not go as I plan. I found it useful to develop small encounters that I could use as random encounters and as side tracks to guide the party or accommodate players who truly want to explore their characters motives. This first set of encounters are designed for characters that are traveling by road. When used as a random encounter table I roll one die eight (1d8), on a 1-6 consult the table on a 7-8 no encounter takes place.
1. Ankle Holes [CR 0 ~ 10XP]
Read to Player’s: The road ahead is covered with leaves and branches as if a great storm had passed through.
The road for the next 1/4 mile is filled with leaves and branches. A dozen ankle holes have been dug throughout the trail. A Wisdom (Perception) Check DC 15 is required to spot the ankle holes. Anyone walking on this stretch of road must make a Dexterity (Acrobatics) check (10) to avoid twisting an ankle. A twisted ankle reduces movement by 1/4. A horse or other beast of burden will automatically fail and be lame for d4+3 days moving at 1/4 movement. A cure wounds spell or 1d3 days of rest will eliminate the penalty. This encounter play’s well as precursor to any ambush style encounters. Award 10xp for successfully avoiding the trap.
2. The road side stand [CR 3 ~ 700XP]
Read to Player’s: Up ahead a small wagon has been set up like a roadside stand. There are five stools set up in front of the wagon. An elderly man sits inside the wagon watching you approach. When you’re close enough the man says “fresh elderberry juice for sale 1 cp a cup.” He follows up with “winter berry wine still good from last year’s harvest 1 sp for a fresh cup.” He has several medium cask propped on a small stand next to.
Of course nothing is as it seems. The old man is a doppelganger looking for easy prey. Players may make a passive Wisdom (Perception) Check against Charisma (Deception +6) [DC 20] to sense something seems out of place. The wine is poisoned with sleeping poison, Constitution save DC 10. The save is made 5 minutes after drinking a cup of wine, each cup drank adds +5 to the difficulty check. Failing a save give the player a disadvantage for 5 rounds before causing her to become unconscious for 30 rounds minus her constitution score. (Fighter has constitution of 15 and fails a save, she would be unconscious for 15 rounds.) His goal is to waylay a few unsuspecting passersby for new identities and gold.
He will make conversation [languages: Common] with anyone who sits at his stand, Wisdom (Insight +3)  against players Wisdom (Insight). If the doppelganger fails three times the player knows something is wrong with this conversation. The conversation generally follows a flow similar to this: a warm inviting greeting, a sales pitch for wine or juice pushing the wine, inquires to where the person is from “Do you live around here?”, family question: “Are you married, have children, pets?”, why they are traveling “Where are you headed?”, what work (profession) do they do and “Does anyone know you where you are going?” You get the point, think socializing at a party full of strangers.
As the person he is talking to reply’s he reads the surface thoughts to direct the conversation (as if concentrating on a spell). While reading the target’s mind, the doppelganger has advantage on Wisdom (Insight) and Charisma (Deception, Intimidation, and Persuasion) checks against the target.
If the players discover that there is something odd and attack the doppelgangers main goal is to escape. He will attempt to run if he can do so without invoking an attack, Speed 30 feet. The doppelganger makes two melee attacks, he has a short sword [1d6 piercing, finesse] and dagger [1d4 piercing, finesse thrown (range 20/60)] within reach that he will use if needed. His first strike will use Slam adding a +6 to hit the first target.
He will attempt to hide from the players and use his shapechanger abilities to change in to a woman. He has several trees, shrubs and fallen logs positioned for just this purpose with spots to hide his gear. Players may make a passive Wisdom (Perception) check DC 18 to notice the doppelgangers hidden item. Active checks have a DC 10. She will be naked and hiding from the players.
Her story will be that she is lost wondering and after drinking some wine she and her companion bought from an old man, Charisma (Deception +6) [DC 20]. She will read the surface thoughts of the player that talks to her first, giving the player a disadvantage to being deceived. She does not know what happened to her companion. The doppelganger can use its action to polymorph into a Small or Medium humanoid it has seen, or back into its true form. Its statistics, other than its size, are the same in each form. Any equipment it is wearing or carrying isn’t transformed. It reverts to its true form if it dies.
If the doppelganger posions all but one appoint he will Surprise Attack. If the doppelganger surprises a creature and hits it with an attack during the first round of combat, the target takes an extra 10 (3d6) damage from the attack. Ambusher. The doppelganger has advantage on attack rolls against any creature it has surprised.
- Doppelganger, Neutral
- AC 14 HP 47 (8d8 + 16)
- STR 11 (+0) DEX 18 (+4) CON 14 (+2) INT 11 (+0) WIS 12 (+1) CHA 14 (+2)
- Condition Immunities charmed
- Senses darkvision 60 ft., passive Perception 11
- Hit: 7 (1d6 + 4) bludgeoning damage
3. Barrel Trap [CR 1 ½ ~ 300XP]
Read to Player’s: A lone crate rest up righted in the middle of the road.
Three Hobgoblin, Mathit, Ektak and Duvla, scouts hide near the side of the road, players can make a Passive Perception DC 12. They were sent to scout raiding routes for the warlord and became lost. They have been lost for several days and are trying to find out where they are so they can get back to their legion. Their intent is to capture a passerby to interrogate them for the information they need.
Their strategy, all be it a simple one, has not worked yet. When anyone stops to investigate the crate Mathit and Ektak open fire with long bows, Ranged Weapon Attack: +3 to hit, range 150/600 ft., and one target. Hit: 5 (1d8 + 1) piercing damage.
Duvla attempts to sneak, Dexterity (Stealth)  against passive Wisdom (Perception), around the side of the road to run out, Speed 30 ft., and snatch the smallest person, using a grapple attack and run back to his companions. So far they have lost on of their team to a group priest on a pilgrimage and killed two merchants. Convinced their plan will work they are trying one more time.
If Duvla cannot grab and go he will draw his longsword and attack trying to knock out one of the players. He gets +3 to hit, reach 5 ft., against one target. With the longsword he deals 5 (1d8 + 1) slashing damage, or 6 (1d10 + 1) slashing damage if used with two hands. If this happens Mathit and Ektak will join the fray the next round. Once per turn, all three can deal an extra 7 (2d6) damage to one creature they hit with a weapon attack if that creature is within 5 feet of an ally that isn’t incapacitated.
If the opportunity presents itself the three will grab the weakest looking players and attempt to flee into the woods.
- Hobgoblin, lawful evil
- AC 18 (chain mail, shield) HP 14 (2d8 + 2)
- STR 13 (+1) DEX 12 (+1) CON 12 (+1) INT 10 (+0) WIS 10 (+0) CHA 9 (−1)
- Senses darkvision 60 ft., passive Perception 10
- Languages Common, Goblin
If the players have never seen Hobgoblins before offer the following description: You see a dark orange skinned man sized gobliniod wearing battle worn chainmail armor. Long dark red-brown unkempt hair pokes out of its helmet. Beneath its beetling brow, yellowish dark brown predator like eyes fixate on you. It has a large blue noise under which its wide mouth grins sporting sharp and yellowed teeth. This creature obviously is relishing the thought of battle.
If you would like the rest of the encounters please download the free pdf here.