Bilbo Baggins’ riddle contest with Gollum in The Hobbit is a legendary battle of wits set in dark caves. These iconic riddles test intellect and courage, captivating Tolkien fans and newcomers alike.

Bag End Mysteries
- Round walls, green doors, adventure’s start. What am I? Bag End
- Maps, sword, pipe room. What am I? Bilbo’s study
- Big meal with toast, eggs. What am I? Second breakfast
- Paved path to round door. What am I? Path to Bag End
- Party tree for farewells. What am I? Shire’s party tree
Gollum’s Riddles
- Soft, brings night, not scary. What am I? Darkness
- Many legs, no prints. What am I? Bookworm
- Roots unseen, taller than trees. What am I? Mountain
- Light, unholdable. What am I? Breath
- Box with no lid, golden inside. What am I? Egg
Misty Mountains
- Echoes, invisible. What am I? Shadow
- Wet, slippery, underground. What am I? Cave stream
- Guards dark paths. What am I? Mountain pass
- Glowing eyes, silent. What am I? Cave predator
- Flickers, banishes night. What am I? Torch
Ring’s Enigma
- Binds with wicked design. What am I? One Ring
- Invisible, tempting trace. What am I? Temptation
- Whispers greed, fear. What am I? Ring’s power
- Forges doom in fire. What am I? Mount Doom
- Corrupts with pride. What am I? Corruption
Gollum’s Tales
- Sly, riddle speaker. Who am I? Gollum
- Nighttime hunger. What am I? Ring obsession
- Dark, frail creature. What am I? Gollum’s form
- Dual voice, kind and cruel. What am I? Gollum’s personality
- Game of riddles in dark. What am I? Riddle battle
Bilbo’s Wit
- Small, outsmarts all. Who am I? Bilbo
- Clever phrase for clues. What am I? Riddle
- Courage in fright. What am I? Bilbo’s bravery
- Sharp mind finds way. What am I? Bilbo’s wit
- Triumph over odds. What am I? Victory

Conclusion
Bilbo’s riddles with Gollum mark his growth from humble hobbit to clever hero. These puzzles blend mystery and courage, offering timeless fun and insight.
