To fly a plane with a tailwheel rather than with a nose-wheel (tricycle gear), you are required to have an endorsement from a Certificated Flight Instructor that you have received the appropriate flight training.
Tailwheel aircraft have their center of gravity behind the main wheels, which makes them more challenging to ground-handle, take-off, and land. It is very important to keep the aircraft aligned with the runway during the take-off and landing phase; if not, exciting things can happen! We explain why these situations occur and how to handle them.
§61.31 Type rating requirements, additional training, and authorization requirements.
(i) Additional training required for operating tailwheel airplanes. (1) Except as provided in paragraph (i)(2) of this section, no person may act as pilot in command of a tailwheel airplane unless that person has received and logged flight training from an authorized instructor in a tailwheel airplane and received an endorsement in the person’s logbook from an authorized instructor who found the person proficient in the operation of a tailwheel airplane. The flight training must include at least the following maneuvers and procedures:
(i) Normal and crosswind takeoffs and landings;
(ii) Wheel landings (unless the manufacturer has recommended against such landings); and
(iii) Go-around procedures.
(2) The training and endorsement required by paragraph (i)(1) of this section is not required if the person logged pilot-in-command time in a tailwheel airplane before April 15, 1991.