October 14 is:
Be Bald and Free Day
national lowercase day
Columbus Day: Celebrated on October 14 in 2024.
On October 12, 1492 – Christopher Columbus reached the Caribbean. It has been reported that from the monarch’s investment of $6000 in Columbus’ first voyage, Spain had a return of $1,750,000 in gold after only one century.
…from Asimov, Isaac. Isaac Asimov’s Book of Facts. New York, Bell Publishing, 1981
Thanksgiving Day in Canada. Thanksgiving has its roots in the European Harvest Festivals where people celebrated an abundant harvest and shared their food within their community.
National Dessert Day
The five most popular desserts in the U.S. are:
Fudge
Chocolate cake-
Chocolate chip cookies 
Brownies-
Ice cream
October 14, 1066 – The Battle of Hastings resulted in William the Conqueror taking over England.
Birthday of William Penn (October 14, 1644), Founder of Pennsylvania and famed leader of the Society of Friends (Quakers). William Penn and his wife, Hannah, are two of only eight people who have been made honorary citizens of the U.S.
Massachusetts Bay Colony enacted the first punitive legislation against the Religious Society of Friends (Quakers) in 1656. The marriage of church-and-state in Puritanism makes them regard the Quakers as spiritually apostate and politically subversive. In all, from 1656 to 1661, at least forty Quakers came to New England to protest Puritan religious domination and persecution. During those five years, the Puritan persecution of Quakers continued, with beatings, fines, whippings, imprisonment, and mutilation.
American Revolutionary War: The United Kingdom’s East India Company tea ships’ cargo were burned at Annapolis, Maryland on this date in 1773.
Birthday of David Dwight Eisenhower (October 14, 1890), thirty-fourth president of the United States. Since his father was named David, the future president had always been called “Dwight”. He changed his name officially – some sources say in high school, some say at West Point.
The loblolly pine tree on the left side of the fairway at the 17th hole at Augusta National Golf Club is known as the Eisenhower Tree. He put his ball in the tree so many times he campaigned to have it removed. It stands to this day. The membership built a cabin for Eisenhower, one of 12 on the course. The cabin, built to Secret Service specifications, still stands on the course and is adorned with an eagle on the front porch.
1912 – While campaigning in Milwaukee, Wisconsin, the former President of the United States, Theodore Roosevelt, was shot and mildly wounded by John Schrank, a mentally-disturbed saloon keeper. With the fresh wound in his chest, and the bullet still within it, Mr. Roosevelt still carried out his scheduled public speech.
The children’s book Winnie-the-Pooh, by A. A. Milne, was first published in 1926.
1947: American test pilot Chuck Yeager became the first person to break the sound barrier.
The Cuban Missile Crisis began in 1962: A U.S. Air Force U-2 reconnaissance plane and its pilot flew over the island of Cuba and took photographs of Soviet missiles capable of carrying nuclear warheads being installed and erected in Cuba.
1964: Baptist minister and social activist Martin Luther King, Jr., was named the winner of the Nobel Prize for Peace, cited for his work involving civil rights and social justice.