- Oct 1 Pennsylvania Turnpike, pioneer toll thruway, opens
- Oct 2 17 German aircraft shot down over England
- Oct 2 British Council receives Royal Charter
- Oct 2 British liner Empress, loaded with refugees for Canada, sunk
- Oct 3 Cincinnati Reds' win Game 2 of the Baseball World Series, 5-2 v Detroit Tigers at Crosley Field; snap 10-game losing streak for NL going back to Game 6 in 1937; Reds win series, 4-3
- Oct 3 France Vichy government proclaims end to Jewish status
- Oct 3 US forms parachute troops
- Oct 4 12 German aircraft shot down above England
Hitler Meets Mussolini
Oct 4 Adolf Hitler and Benito Mussolini confer at Brenner Pass in the Alps
- Oct 4 French Vichy regime proclaims end of "Statute of the Jews"
- Oct 6 Zoological Gardens opens at Sloat & Skyline Boulevards in San Francisco, California
- Oct 7 World War II: the McCollum memo proposes bringing the U.S. into the war in Europe by provoking the Japanese to attack the United States.
- Oct 8 Baseball World Series: Cincinnati Reds beat Detroit Tigers, 2-1 at Crosley Field for 4 games to 3 series win; Reds second championship
- Oct 8 German troops occupies Romania
'Hitler Will Have to Break Us or Lose the War'
Oct 14 Balham tube station in London is bombed by the German Luftwaffe during the Blitz, killing 64-66 people
The Great Dictator
Oct 15 "The Great Dictator", a satiric social commentary film by and starring Charlie Chaplin released
- Oct 15 -16] Heavy German air raid on London, 400 killed
- Oct 15 London's Waterloo Station bombed by German luftwaffe
- Oct 16 Benjamin Oliver Davis Sr. is promoted to brigadier general, the first African-American person to become a general in the US military
Warsaw Ghetto
Oct 16 Warsaw Ghetto is formed by German Governor-General Hans Frank
Hitler Meets Petain
Oct 24 Adolf Hitler meets the Head of the French State Marshal Philippe Pétain
- Oct 24 Japan eliminates US terms (strike, play ball) from baseball
- Oct 24 Protestant churches protest against dismissal of Jew civil servants
- Oct 24 US Fair Labor Standards of 1938 comes into effect - minimum wage, 44 hr week
- Oct 25 Benjamin O Davis Sr. becomes 1st African American general in US Army
- Oct 25 Vernon Duke and John Latouche's musical "Cabin In The Sky" opens at the Martin Beck Theatre, NYC; runs for 156 performances
- Oct 26 The P-51 Mustang makes its maiden flight.
- Oct 28 Greece successfully resists Italy's attack
- Oct 28 Meeting between Adolf Hitler and Benito Mussolini in Florence, Italy
- Oct 29 Secretary of War Henry L Stimson draws the 1st number - #158 - in the 1st peacetime military draft in US history
Panama Hattie
Oct 30 Cole Porter's musical "Panama Hattie" opens at 46th Street Theatre, NYC; runs 501 performances
- Oct 31 Battle of Britain, fought between the RAF and Luftwaffe over the English Channel and southern England, ends with a British victory
Warsaw Ghetto
Oct 31 Deadline for Warsaw Jews to move into the Warsaw Ghetto
Admirals
Aviators
Gangsters
Generals
Industrialists
Suffragists