1906 – Birth of Jacqueline Cochran, pioneer American aviator, considered to be one of the most gifted racing pilots of her generation. She was an important contributor to the formation of the wartime Women’s Auxiliary Army Corps (WAAC) and Women Airforce Service Pilots (WASP).  In May of 1953 she became the first woman to break the sound barrier.

1908 – The Wright brothers fly for the first time since 1905, at Kitty Hawk. Wilbur pilots the 1905 Flyer III, modified so that the pilot and a passenger can sit erect, on a flight of just over 1,000 feet.

1910 – Glenn Curtiss flies from Albany NY to New York City, a then-epic flight of about 150 miles. This could loosely be credited as the first air mail flight, for he unofficially carried a letter from Albany’s mayor to the mayor of NYC.

1912 – Lieutenant Commander Charles Samson becomes the first person to fly an aircraft off the deck of a moving ship. He takes off in a Short S.38 from the deck of HMS Hibernia in Weymouth Bay.

1923– 2-3 – Kelly MacReady complete the first non-stop flight from New York to Los Angeles, in 27 hours in a Fokker T-2.

1927 – (20-21) Charles Lindbergh flies across the Atlantic nonstop from New York City to Paris. It is the first solo transatlantic flight. In his Ryan monoplane Spirit of St. Louis, he covers 3,600 miles in 33 hours, 29 min and wins the Orteig Prize of $25,000.

1932 – Amelia Earhart, flying a Lockheed Vega, becomes the first woman to make a solo flight across the North Atlantic, flying from Harbour Grace in Newfoundland to Derry in Northern Ireland in 14 hours 54 min

1952 – Trans World Airlines (TWA), British Overseas Airways Corporation (BOAC) and Air France launch the world’s first scheduled tourist-class flights on their transatlantic routes from New York, London and Paris.

1960 – 1960 U-2 incident: A CIA Lockheed U-2A, 56-6693, Article 360, flown by Francis Gary Powers is shot down by a SA-2 (Guideline) missile near Degtyarsk in the Soviet Union during an overflight codenamed Operation GRAND SLAM, the twenty-fourth and most ambitious deep-penetration flight of the U-2 program. Powers parachutes down and is captured. Soviet Premier Nikita Khrushchev announces on 7 May to the Supreme Soviet of the Soviet Union, and thus the world, that a “spyplane” has been shot down but intentionally makes no reference to the pilot. Powers is later produced in a ‘show trial’. On 10 February 1962, twenty-one months after his capture, Powers is exchanged along with American student Frederic Pryor in a spy swap for Soviet KGB Colonel Vilyam Fisher (aka Rudolf Abel) at the Glienicke Bridge in Berlin, Germany.

1965 – A Lockheed YF-12 sets a new international airspeed record of 2,070 mpg (3,331 km/h).

1998 – The 100th and final B-1 B was delivered.

2011 – (Overnight) In Operation Neptune Spear, two modified United States Army UH-60 Blackhawk helicopters of the 160th Special Operations Aviation Regiment (Airborne) carry United States Navy SEALs of the United States Naval Special Warfare Development Group from Jalalabad, Afghanistan, to Abbottabad, Pakistan, where they attack the compound of al-Qaeda leader Osama bin Laden, and kill him and four others in the compound. One Blackhawk crashes during the assault, but there are no serious injuries to any Americans, and the remaining Blackhawk and a CH-47 Chinook helicopter fly the SEALs and bin Laden’s body back to Afghanistan.

2013 – A Boeing X-51A WaveRider unmanned scramjet demonstration aircraft detaches from a Boeing B-52H Stratofortress and reaches Mach 4.8 (3,200 mph; 5,100 km/h) powered by a booster rocket. It then separates cleanly from the booster, ignites its own engine, accelerates to Mach 5.1 (3,400 mph; 5,400 km/h), and flies for 240 seconds – setting the record for the longest air-breathing hypersonic flight in history – before running out of fuel and plunging into the Pacific Ocean off Point Mugu, California, after transmitting 370 seconds of telemetry. The flight – the fourth and last planned X-51A test flight and the first successful one – completes the X-51 program.^[1][2][3]

The above is a partial list of aviation events that took place in the month of May.  A more complete listing can be found here.