Plain English Meaning
An airplane that rests on two main wheels at the front and a small wheel under the tail, so the nose points up when it's parked or taxiing.
Full Definition
Describes an airplane with a landing gear configuration consisting of two main wheels forward of the center of gravity and a small wheel at the tail, causing the airplane to sit nose-high on the ground.
Context Anchor
Seen in takeoff, landing, taxi, and ground-control discussions for tailwheel airplanes, especially when explaining unwanted sharp turns on the ground.
Derivation
Named for the small wheel under the tail. Sometimes called a 'taildragger' for the same reason. The contrast is the 'tricycle-' airplane, which has a up front instead.