January 7, 1911
Just over seven years after the Wright Brothers’ pioneering flight at Kitty Hawk, the first bulk delivery of newspapers via a plane took place in California. French barnstorming pilot Didier Masson agreed to transport several bundles of the Los Angeles Times from Los Angeles to San Bernardino. The bundles were strapped to the wings of his Curtiss-Farman biplane, which was nicknamed “Pegasus.”
The 24-year-old pilot (heralded as “Aerial Newsboy” in one press account) planned to depart from Los Angeles at around seven o’clock that morning for a 60-mile (96.6-kilometer) flight that would entail stopping in Pomona en route to drop off some newspapers there and then reaching San Bernardino by 10:00 a.m. to deliver the remaining load. The flight, however, did not go exactly as planned.
Masson flew out of Los Angeles at 7:05 a.m. but ended up not making his scheduled stop in Pomona. Due to a navigational error, he missed flying over Pomona and instead found himself lost in the hills north of there. Masson tried to get his bearings, dodging canyons and cliffs while also dealing with strong winds. Ultimately, however, his plane’s fuel ran out and the aircraft crash-landed on the ground below. Masson was uninjured, but one of the plane’s oil tubes broke.
What followed was an extended effort to get in contact with his mechanic, who finally did make it to the site of the landing to replace the damaged tube. With the plane repaired and refueled, Masson took to the skies again and resumed his flight to San Bernardino. He arrived at Association Park in that city about five-and-a-half hours after leaving Los Angeles and unpacked the newspapers he had brought with him. He subsequently spent time there in the city enjoying lunch at the local Elks Club and performing an aerobatics show.
For more information on Didier Masson and his airborne achievements, please check out https://en.wikipedia.org/wiki/Didier_Masson.
Transportation History 
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