A blog about the history of street performers in Mallory Square, Key West.


Welcome to the Mallory Square Street Performers blog! Here you’ll find everything you ever wanted to know about Mallory Square’s famous street performers. You’ll be able to find out who we are, what we do, and where we come from. We’ve also set up a forum so that you can share your thoughts and opinions with other Mallory Square fans around the world.

The origins of Mallory Square street performers started over 200 years ago when the first drummers started coming to Key West and performing for tourists in the streets. The tradition has been passed down through the generations and now some of us have been doing it for nearly 30 years.

Mallory Square is a historic place in Key West where many famous people came to visit while they were alive including Ernest Hemingway, Harry Truman, Tennessee Williams, Judy Garland and more recently Princess Diana when she visited with her sons William and Harry back in 1985 during their tour of America.

It is hard to remember the first time I saw the famous street performers of Mallory Square. But once they grabbed my attention, they never let go.

I was a young boy when I first visited Key West with my family in the early 1970s. My memories are faded – perhaps from the sun and countless hours at Higg’s Beach – but I do remember that even then Mallory Square was a must stop for tourists and locals alike.

The square itself was not much to look at: a weathered, bare-bones concrete building that was anything but elegant; an open-air market selling everything from handmade jewelry to cheap souvenirs; and a food court that featured such island favorites as grouper sandwiches and conch fritters.

But what made the place stand out were its remarkable performers, who dared to climb masts, swallow fire and jump through flaming hoops whenever the sun set in the Florida Keys.

The square has changed since those days, now boasting elegant shops and fine restaurants. But every day at sunset, its streets are still filled with talented young men and women who continue to practice the ancient art of entertaining people on the street corner.

I hope you enjoy – and perhaps even learn something from – this site dedicated to these remarkable people

History of Mallory Square Street Performers, Key West

In the early days of Key West as a port city, the waterfront was the home of sailors and ships’ captains. The entrepreneurial spirit of these men provided entertainment for the families that remained in Key West while their husbands and fathers were on long voyages. As time went on, local fishermen began selling fresh catch at the docks. Sailors and fishermen would pass time by telling tall tales, jokes and singing sea shanties. At sunset, they would gather at Mallory Square to recount their adventures of the day.

Over time, more tourists arrived in Key West, and Mallory Square became an attraction for visitors as well as residents. Still today, locals and visitors alike gather at Mallory Square to watch the sunset – among other things!

Mallory Square street performers are a part of the island culture that makes Key West unique, and they have been performing in Mallory Square since the 1960s. For generations of tourists and locals alike, these performers are a part of why Key West is so famous for its vibrant, quirky charm.

Mallory Square has been known as a center for entertainment and events since the mid-1800s. The Civil War saw the Union Army setting up camp on the square in 1822, where it remained until 1825. At the turn of the century, Mallory Dock was considered one of the busiest ports in the Florida Keys. In 1942, the U.S. Navy established a naval base on what is now Naval Air Station Key West, which was used to house troops during World War II and beyond.

In 1960, after years of being used as an airport runway and storage facility, Mallory Dock was renovated into a cruise ship port with shops lining the waterfront and maintaining its status as a popular destination for both locals and visitors alike. Today there are more than 100 local vendors who sell their wares along the waterfront seven days a week from 9AM to 5PM every day except Christmas Day.

The sunsets in Key West are legendary, but the real show starts after they dip below the horizon. The Pier at Mallory Square is home to a bustling assortment of street performers and vendors, who set up shop daily to create the world-famous Sunset Celebration.

From fire jugglers to sword swallowers, from psychics to illusionists, from musicians to comedians, you can find just about everything in the Square. And it’s not just people showing off their talents: if you want a caricature of yourself or even a quick pastel portrait, you can get that as well.

But this isn’t all about transient entertainment. At sunset you can also find artists and craftsmen selling their wares, from woodcarvings to handmade jewelry.

The Mallory Square Sunset Celebration is part of what makes Key West so special. It’s a vibrant mix of people and culture, art and history. It’s something everyone should experience at least once in their lives!

Mallory Square is a historic waterfront plaza in Key West, Florida. Located on the north side of the island, Mallory Square is home to shopping, restaurants, and popular sunset celebrations.

The square was named in honor of John Pendleton Mallory, a farmer and businessman who served as an Alabama representative in the U.S. House of Representatives from 1833 to 1843. He became an early proponent of Key West’s annexation by the United States from Spain following the Adams-Onís Treaty of 1819.

The square’s modern history began when it was redeveloped into a tourist zone during the 1960s, with its location adjacent to Key West Bight playing a major role in its popularity with visitors and locals. The square has since become known for its sunset celebration that draws thousands to watch the sun set over Key West Harbor every day.


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