Rolling scenic hills dot landscapes across the globe and are natural fits for starting an adventure. They bridge grasslands and mountains and make great second environments to explore in your adventures. These tables are here to provide you with inspiration or random encounters to drop on your players and add some more life to the hilly environments in your worlds!

Sources

Each encounter focuses on a monster from throughout the D&D 5e library; to see what book or source they come from, you can consult the Book column. The sources unabbreviated sources are Basic Rules (BR), Monster Manual (MM), Mordenkainen Presents: Monsters of the Multiverse (MPMM), Icewind Dale: Rime of the Frostmaiden (RoF), Out of the Abyss (OoA), Volo’s Guide to Monsters (VGM), and Storm King’s Thunder (SKT).

Hill Random Encounters

The following table provides random encounters for parties playing in various “tiers” of gameplay; they generally reflect encounters you can sculpt to work for tables within a level range. The Low-tier can work for levels 1-4, Mid-tier for levels 5-11, and the Upper-tier for levels 12+.

Low-Tier Adventuring Random Encounter Table

            d20
            Book
            Encounter
            
            1
            BR
            1d12+4 sheep fleeing their firbolg shepherd
            
            2
            BR
            1d4+3 bandits lurking by a fake caravan wreck to ambush people coming to help
            
            3
            BR
            A nest of 1d6+1 stirge in the dense canopy of the wooded foothills
      
            4
            BR
            1d6+2 elk grazing peacefully, unaware of the two scouts about to shoot
            
            5
            BR
            1d4+3 red kobold bandits working out of a hilltop outpost
            
            6
            BR
            Two swarms of ravens summoned as a warning for trespassers nearing a lair
            
            7
            BR
            Two giant goats and their druid goatherd resting on a cozy hillside
            
            8
            BR
            1d4+2 goblins, two of whom ride worgs, on a reconnaissance mission
            
            9
            BR
            A dire wolf leading a pack of 1d4 wolves
            
            10
            BR
            Two hippogriffs attacking two lost children that moved too close to their nest
            
            11
            MPMM
            A nilbog performing for a goblin bosses and 1d4 goblins
            
            12
            BR
            Two giant boars aggressively sparring
            
            13
            BR
            An ogre, goblin, and their hobgoblin leader on a quest for redemption
            
            14
            MM
            A rogue pertyon terroizing a traveling band of musicians
            
            15
            MPMM
            Two shadow mastiffs carrying a message for a night hag to her sister
            
            16
            BR
            A bandit captain and their 1d4+1 bandits reveling after a successful robbery
            
            17
            BR
            Two giant vultures harrying a gnome hiding inside a fallen hollowed out tree
            
            18
            MM
            A pair of half-ogres and their orc bounty hunter companion
            
            19
            BR
            A group of 1d4+2 harpies nesting in a ruined watchtower overlooking the hills
            
            20
            MPMM
            	A red kobold dragonshield, scale sorcerer, and 1d4 winged kobolds

Mid-Tier Adventuring Random Encounter Table

            d12
            Book
            Encounter
            
            1
            MPMM
            A shadow mastiff alpha leading 1d4+1 shadow mastiffs in a human hunt
            
            2
            BR
            Three werewolves and their wererat companion running a horrific butcher
            
            3
            BR
            An ettin and a hill giant fighting over who gets eat the felled giant eagle
      
            4
            BR
            A wereboar with their druid companion and two giant boar pack animals
            
            5
            BR
            1d4+1 bulettes lurking beneath the hills for prey
            
            6
            SKT
            Two hill giants preparing to make stew of their three goblin prisoners
            
            7
            MPMM
            Two tanarukks leading a band of 1d4+3 orc raiders
            
            8
            BR
            A werebear, weretiger, wererat, werewolf, and wererat adventuring party
            
            9
            MPMM
            An annis hag and an ogre dragging a bag of terrified haflings back to their lair
            
            10
            BR
            Two wyverns hunting for large beasts across the hillsides
            
            11
            SKT
            Two stone giants creating a massive statue of their deity with heavy stone
            
            12
            BR
            A yong copper dragon under attack from a young red dragon rival

Upper-Tier Adventuring Random Encounter Table

            d6
            Book
            Encounter
            
            1
            MPMM
            Two dire trolls and 1d4 trolls ruling over a critical bridge and its watchtowers
            
            2
            BR
            An adult red dragon and its 2d6+3 red kobolds attacking a fort
            
            3
            MM
            An adult red draoclich leading an squad of 2d12 zombies and 2d6 skeletons
      
            4
            MPMM
            A zaratan destroying a nearby city who expanded on top of it accidently
            
            5
            BR
            A tarrasque released into the wild progressing rapidly towards a dense city
            
            6
            BR
            An ancient red dragon whos dominion expands beyond their mountains