Duval Street: The Longest Street in the World

March 19 - Summer 2021

Custom House Museum | Bryan Gallery

Duval Street is the most recognized street in the Florida Keys, serving as the island’s core cultural and historical artery.  It is whimsically dubbed ‘The Longest Street in the World’ since it stretches one-and-a-quarter miles from the Gulf of Mexico on the north end all the way to the Atlantic Ocean on its southern edge.  Home to architectural gems such as St. Paul’s Church, The Strand Theater, the San Carlos Institute and the Southernmost House, it has also hosted iconic bars and restaurants including Sloppy Joe’s, the Monster, Pepe’s Cafe, Shorty’s Diner, Delmonico and countless more.

In spite of its legendary reputation, Duval Street had a very humble beginning.  When Key West was settled in the 1820s, Whitehead Street emerged as the central road it ran from the seaport down to the original Key West Lighthouse near today’s Southernmost Point.  Duval, named for Florida’s first territorial governor, William Pope Duval, was a minor thoroughfare since a sizeable area around the northern end was a saltwater pond and the southern end had yet to be cleared of trees.  A few years prior to the outbreak of the Civil War, the city decided to fill in the pond so Duval Street could run unrestricted through the center of downtown.

This modification signaled a turning point for Duval Street.  Not only did Duval grow in length, there was also an increased importance to wreckers, spongers, cigar manufacturers, tourists and residents who built grand houses, churches, places of business, restaurants and saloons.

A few of the remarkable objects that will be on display include a 100-foot section of the “Sea to Sea” Rainbow Flag that was spread 1.25 miles from the Gulf to the Atlantic in 2003 and a silk menu from a luncheon held at the Russell Hotel in honor of Ulysses S. Grant’s visit to the island in 1880.  Intaglios illustrating several Duval Street buildings created by Cuban-American artist Mario Sanchez will also be presented to visitors.

“So much of our island’s heritage is connected to that one-and-a-quarter mile thoroughfare,” adds Convertito.  “By mounting this exhibition, the Society hopes to enlighten visitors on the historical importance of Duval Street that extends well beyond its bars and restaurants; we must honor the people, the buildings and events that shaped our story.”

Related Projects