Rolls was also a pioneer aviator and initially, balloonist, making over 170 balloon ascents. He was a founding member of the Royal Aero Club in 1903 and was the second person in Britain to be licensed to fly by it. In 1903 he also won the Gordon Bennett Gold Medal for the longest single flight time.
By 1907 Rolls' interest turned increasingly to flying, and he tried unsuccessfully to persuade Royce to design an aero engine. In 1909 he bought one of six Wright Flyer aircraft built by Short Brothers under licence from the Wright Brothers, and made more than 200 flights. On 2 June 1910, he became the first man to make a non-stop double crossing of the English Channel by plane, taking 95 minutes – faster than Blériot. For this feat, which included the first East-bound crossing of the English Channel, he was awarded the Gold Medal of the Royal Aero Club. There is a statue to commemorate the flight in the town square at Monmouth and at Dover.