• Question: What starts with a “P” and ends with an “E”, yet has thousands of paths in between?
  Answer: A Map.
• Question: I’m always on the road, yet never moving. What am I?
  Answer: A Milestone.
• Question: What has keys but can’t open locks, and roads but can’t be driven on?
  Answer: A Keyboard.
• Question: What can travel around the world while staying in a corner?
  Answer: A Stamp.
• Question: What goes up and down the road without moving?
  Answer: The Temperature.
• Question: I speak without a mouth and hear without ears. I have no body, but I guide you on the road. What am I?
  Answer: A GPS.
• Question: What has cities, but no houses; forests, but no trees; and rivers, but no water?
  Answer: A Map.
• Question: What belongs to you but others use it more than you do on the road?
  Answer: Your Name.
• Question: What can be cracked, made, told, and played while traveling on the road?
  Answer: Jokes.
• Question: I have keys but no locks. I have a road but no pavement. What am I?
  Answer: A Keyboard.
• Question: What has a head and a tail but no body, and travels on the road?
  Answer: A Coin.
• Question: What has a neck but no head, and travels on the road?
  Answer: A Bottle.
• Question: What has a foot but no legs, and travels on the road?
  Answer: A Ruler.
• Question: What travels the world while staying in one corner?
  Answer: A Stamp.
• Question: What can be full or empty, yet always holds something while traveling on the road?
  Answer: A Suitcase.
• Question: What has a bed but never sleeps, and travels on the road?
  Answer: A River.
• Question: What has keys but can’t open locks, and roads but can’t be driven on?
  Answer: A Keyboard.
• Question: What runs around a city but never moves?
  Answer: A Fence.
• Question: What has a bottom at the top?
  Answer: Your Legs while walking.
• Question: What is a room you can enter but never leave while on the road?
  Answer: A Traffic Jam.

• What is a road’s favorite type of music?
• Why did the road go to school?
• What did the road say to the impatient driver?
• Why was the road always happy?
• What did the road say to the pedestrian?
• What did the streetlight say to the road?
• Why did the road feel tired?
• What did the road say to the pothole?
• Why did the road cross the city?
• What’s a road’s favorite movie genre?
• Why did the road turn red?
• What did the road do on its day off?
• Why did the road feel lonely?
• What did the road say to the highway?
• Why did the road feel overlooked?
• What did the road say to the sidewalk?
• Why did the road feel jealous?
• What did the road say to the bridge?
• Why did the road feel proud?
• What did the road say to the traffic cone?

Another Road riddles

• Why did the road feel tired?
• What did the road say to the pothole?
• Why did the road cross the city?
• What’s a road’s favorite movie genre?
• Why did the road turn red?
• What did the road do on its day off?
• Why did the road feel lonely?
• What did the road say to the sidewalk?
• Why did the road feel jealous?
• What did the road say to the bridge?
• Why did the road feel proud?
• What did the road say to the traffic cone?
• Why was the road feeling nostalgic?
• What did the road say to the detour sign?
• Why did the road feel conflicted?
• What did the road say to the speed bump?
• Why did the road feel misunderstood?
• What did the road say to the construction worker?
• Why did the road feel relieved?
• What did the road say to the GPS?

• What is full of holes but can still hold water? (Answer: A road with potholes)
• What has lanes but no traffic? (Answer: A deserted road)
• What stretches miles but never tires? (Answer: A long highway)
• What gets longer when pulled, fits snugly between cars, yet never tangles? (Answer: A road divider)
• What has a beginning but no end? (Answer: A road)
• What has curves but never moves? (Answer: A winding road)
• What is traveled every day but never arrives? (Answer: A commuter’s journey)
• What can be paved but never laid? (Answer: A road)
• What has lines but can’t be read? (Answer: Road markings)
• What is black and white and red all over? (Answer: A newspaper thrown on the road)
• What connects one place to another yet never moves? (Answer: A road)
• What is always ahead of you but never moves? (Answer: The road)
• What can be crossed but never touched? (Answer: A road)
• What has shoulders but can’t shrug? (Answer: A road)
• What is wide at one end, narrow at the other, and full of surprises? (Answer: A winding road)
• What is made of stone yet constantly changing? (Answer: A cobblestone road)
• What has cracks that can’t be fixed? (Answer: A broken road)
• What can be taken but never stolen? (Answer: A road trip)
• What has lanes but no runners? (Answer: An empty street)
• What is paved with good intentions? (Answer: The road to hell)

Getting over with Road riddles

• What is always underfoot but never walks? (Answer: A road)
• What is smooth in the day but bumpy at night? (Answer: A road)
• What is long and winding and leads to unexpected places? (Answer: A scenic route)
• What has a fork but isn’t for eating? (Answer: A fork in the road)
• What is traveled by vehicles but never arrives at a destination? (Answer: A loop road)
• What is wide enough for two but often taken alone? (Answer: A single-lane road)
• What is made of concrete but never grows? (Answer: A paved road)
• What is measured in miles but has no length? (Answer: A road trip)
• What is traveled by many yet owned by none? (Answer: A public road)
• What is straight but not narrow? (Answer: A highway)
• What has intersections but no buildings? (Answer: A crossroads)
• What is filled with turns and twists but has no plot? (Answer: A winding road)
• What is marked by white lines but never speaks? (Answer: A road)
• What is smooth when new but rough with age? (Answer: A worn-out road)
• What is made of black tar but isn’t sticky? (Answer: A road surface)
• What is paved with yellow bricks? (Answer: The road to Oz)
• What is traveled by both wheels and feet? (Answer: A pedestrian-friendly road)
• What is traveled by day but avoided at night? (Answer: A dangerous road)
• What is made for driving but sometimes walked? (Answer: A road)
• What is filled with signs but has no words? (Answer: A road)