Originally Posted by Office of the Chief Counsel, FAA
As noted above (14 CFR 61.1(b)(3)), cross country flight time is defined as time acquired during a flight that includes a point of landing that is at least a straight-line distance of more than 50 nm from the original point of departure, not the original point of any flight leg. There is no requirement that any specific leg must be 50 nm. Moreover, a cross-sountry flight may include several legs that are less than a straight-line distance of more than 50 nm from the original point of departure. Nevertheless, at least one leg of the cross-country flight, however long by itself, must include a point of landing that is at least a straight-line distance of more than 50 nm from the original point of departure (i.e. of the flight, not of that particular leg). (all emphasis is mine - ets)
Given the above analysis, the answer is each cross-country flight used to meet the aeronautical experience requirements under 14 CFR 61.1(b)(3) must include one leg that includes a landing that is at least a straight-line distance of more than 50 nm from the original point of departure.
This response was prepared by Adrianne Wojcik, an Attorney in the Regulations Division of the Office of the Chief Counsel, and has been coordinated with the General Aviation Division of Flight Standards Service.