OCTOBER 19:

1864 St. Albans, Vermont - Confederate States of America Lt. Bennett Young leads 25 Confederate Civil War fugitives hiding in Montreal to St. Albans, where they rob three banks of $200,000, and kill one person, before escaping back across the border to St-Jean; thirteen are arrested a few days later, and held for extradition, but are released on a technicality by a Montreal police magistrate; northernmost engagement of the US Civil War.

October 19, 1841:  On this day Tallahassee Seminole Chief Tiger Tail (Thlocko Tustennuggee) surrendered to American forces based on the intervention of Seminole Chief Alligator (Hallpatter Tustennuggee).  Three months later Tiger Tail escaped from government detention in Fort Brooke.

October 19, 1607:  English settlers officially found "the other" English colony on North America. Unlike Jamestown, Popham is settled by just men and boys. Popham, northeast of modern Portland, Maine, is established on the bluffs overlooking the spot where the Kennebec River flows into the ocean. The colony lasts only a little over one year. The colony's second leader returns to England, taking the settlers with him, when he inherits a sizeable estate in England.
 
 
 

BACKGROUND:
 

From http://members.aol.com/Wsresort/history.html
 

... on Egmont Key in 1858 at the conclusion of the Billy Bowlegs War, the final Indian War in Florida. Billy Bowlegs was the last Seminole Indian chief remaining in South Florida. He surrendered with his weary band of 138 followers in Fort Myers on May 4, 1858. The tribesmen were transported to Egmont Key for their final Florida rendezvous before being shipped across the Gulf of Mexico to a reservation in Arkansas. One proud Seminole warrior - Tiger Tail - could not endure the humility of being taken from his native Florida. In the morning, the Indians were to leave Egmont Key, Tiger Tail ground up a quantity of finely ground glass and swallowed it with a glass of water. Tiger Tail's suicide tragically ended the era of Florida Indians.