1925 – A train with six water cars derailed overnight at Spanish Harbor near Big Pine Key. A wrecking train was dispatched immediately to clear the tracks, and traffic was restored by dawn.

1938 – Toll receipts showed that 1,821 automobiles, carrying 3,632 passengers, had traveled the Florida Keys Overseas Highway over the Christmas weekend.

1940 – The Cuban-American fraternal order Orden de Caballeros de Martí began a three-day state convention at the Key West chapter’s lodge at 919 Elizabeth Street.

1935 – Despite the air temperature being a chilly 52 degrees, visitors from the north enjoyed swimming in the waters off Key West’s Rest Beach.

1975 – Monroe County Sheriff’s deputies, Navy personnel, and volunteers were working to remove 6,000 pounds of baled marijuana that washed ashore along Boca Chica and other keys. One bag was labeled “Bogota,” but there was no evidence of a boat that dumped the $2.5 million haul.

1955 – The home of Angel Delgado at 1010 Washington Street was chosen as having the best display in the Key West Junior Chamber of Commerce’s Christmas lighting contest. The home of Everett Hall at 3 Hibiscus Lane placed second.

1930 - The Key West Woman’s Club, the Salvation Army, and the U.S. Army distributed 291 Christmas dinners to the poor of the city.

Enjoy free concerts at the Key LargoLibrary branch in the Upper Keys

Enjoy free concerts at the Islamorada Library branch in the Upper Keys

1891 – José Martí, the leading Cuban independence advocate, arrived at Key West from Tampa for his first visit to the island. He rallied Key West’s Cuban exile community to support the overthrow of Spanish rule over their island nation.

The Monroe County Public Library has lots of ways to help you reach your New Year's Resolutions - at no cost.

1955 – Florida Greyhound buses resumed service after a drivers’ strike. Airlines, and even cab drivers, had been able to get some travelers from Key West to Miami, but there was particular concern in the Keys that Navy personnel would not have been able to travel for the holidays.

1935 – The Cortez Cigar Co. building on Ann Street in Key West was destroyed by fire. The first alarm sounded at 10 a.m. and all the city’s firefighters arrived to battle the blaze, but the flames spread too quickly to be contained. Chief Harry Baker thought the fire was set intentionally.

1897 – Schooners leaving Key West were given warning shots by the U.S.S. Maine as a command for them to halt. The vessels were boarded by officers from the battleship and searched for arms and ammunition that might be used to illegally supply revolutionary forces in Cuba. None were found.

The Marathon Library Branch is presenting musicians, authors and more as part of its 2026 Performance Series.

1985 – The 297-foot ocean freighter Eagle was sunk as an artificial reef in 100 feet of water off Islamorada. The project was sponsored by the Florida Keys Artificial Reef Association and the Keys Association of Dive Operators.

Enjoy free concerts at the Big Pine Key Library.

1974 – Keys shrimpers were experiencing a significant economic downturn as shrimp prices had dropped 39 percent over the previous year, while the cost of fuel was up 50 percent.

1985 – The new Seven Mile Bridge and the Long Key Bridge, both completed in 1982, were suffering from structural problems. Guardrails on the Seven Mile Bridge were spalling, and elements of the underside were deteriorating. Issues with the Long Key Bridge required that a model of it be built in Tallahassee so engineers could conduct stress tests. 

Enjoy free concerts at the Key West Library's Music in the Palm Garden series.