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.

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.

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.

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. 

1940 – Author Thelma Strabel moved into her new Key West home at 400 South Street by the Southernmost Point. Strabel wrote the novel “Reap The Wild Wind,” a story about island wreckers that was later made into a movie.

1957 – Construction started on the Blue Lagoon Motel at the corner of Sigsbee Road and North Roosevelt Boulevard in Key West.

1995 – Bicycling magazine named Key West the most dangerous city in the U.S. for bicyclists. Florida DOT Bicycle/Pedestrian Coordinator Dan Burden noted, “It’s 19 times more dangerous to ride in Key West than anywhere else in the nation.”

1985 – The widening of U.S. 1 to four lanes through Marathon began with the stretch between 105th to 122nd Streets. The entirety of the road, from 41st Street to Coco Plum Drive, would eventually be done across multiple phases.

2008 – Due to the year-long economic down-turn, Florida Keys marinas were struggling to fill slips. Many were on the verge of bankruptcy.

1960 – After five years of service, the Key West-Havana ferry made its final crossing from Cuba. The official reason for the suspension of service was a lack of patrons, but it also came as tensions were increasing between the U.S. and Fidel Castro’s new government.  

1962 – As tensions with Cuba increased, the FAA constructed a temporary control tower at Key West International Airport overnight. In addition, many military personnel arrived over the weekend.

1985 – The Old Island Restoration Commission approved plans for the conversion of Key West’s De Poo Hospital at 918 Southard Street to Southard Square Condominiums. The redevelopment would blend the existing structures and new construction.

1985 – The City of Key West listed privately owned areas of the Key West salt ponds as desirable for purchase by the State of Florida under its Conservation and Recreation Lands (CARL) program. Many residents considered the ponds to be the last remaining natural expanse on the island.

1951 – The City Planning Board approved a zoning change for Dairy Queen to build an ice cream store on United Street near White Street.

1906 – John Lowe Jr. had a wholesale and retail lumber business, grocery store, ship chandlery and marine railway at the corner of Elizabeth and Greene streets.

1954 – The Florida Keys were undergoing a building boom: The permit for a two-bedroom $5,800 CBS home at Marathon was the 800th issued by Monroe County for new construction in unincorporated areas in two years.

1925 – A celebration was held for the opening of the Boca Chica bridge, the first step in the new Overseas Highway being built through the Florida Keys. A “mammoth motorcade” left Key West, crossed Stock Island and then traversed the new bridge to Rocky Point on Boca Chica Key for the celebration.

1994 – More than 17,000 Cuban refugees had crossed the Florida Straits during the month. It was the largest Cuban exodus since the 1980 Mariel boatlift.

1951 – Developer Joe Sirugo agreed to sell 3,500 cubic yards of marl to the City of Key West. It would help satisfy the city’s need of 10,000 yards of marl to fill United Street between Leon and George streets and to fill George Street along the site of the new city housing project.

1945 – Blas Zarate of the White Inn on Division Street (now Truman Avenue) in Key West was arrested for selling beer on a Sunday, and customer Harvey Stirrup was charged with consuming beer on Sunday. The men were given bonds of $250 and $25, respectively.