The story of hippies and Mallory Square is one of transition, Mallory Square development, and local acceptance and rejection.

Hippies came upon the scene in the 1960’s. They moved big time into the 1970’s.

A hippie was a person of unconventional appearance, typically having long hair, associated with a subculture involving a rejection of conventional values and the taking of hallucinogenic drugs. They wanted to understand everything, understanding being the operative word. Some traveled to India in search of enlightenment.

A simple description would be they believed in live and let live, love, and had a concern about others. Love led to many engaging in group sex and communal living.

Mallory Square has always been and still is a spectacle of the sun sinking into the Gulf of Mexico. Today a festival featuring street performers, arts, crafts, and food carts.

It was not so back when. Back when being the 1950’s when it was first discovered that the setting sun could be enjoyed from Mallory Square.

Rex Brumgart operated a concession stand at South Beach. It was a Sunday evening. He was bored. He packed a small carry on with an ice-cold martini shaker, some Triscits, a wedge of brie, and a spot of caviar. Under one arm, a folding chair and a small folding table.

Mallory Square that evening not even close to the Mallory Square of today. Old docks consisting of rotting water-soaked planks. Mud everywhere. It was the site of the Champion Seafood warehouse and a major shrimp boat mooring.

He probably nodded to the many fishermen about. Numerous cats were running around sniffing the fishermen’s bait.

Brumgart went to the end of the rotting dock, opened his chair and table, and set out his martinis and food. He proceeded to get smashed a bit. While doing so, the sunset was slipping closer to the horizon.

The sunset that evening was spectacular. A luminous gold ball.

As the sun broke the horizon, Brumgart stood, lifted a toast, and shouted “Bravo!”

Brumgart continued his evening visits. Initially, fishermen joined him. Then locals. One by one. Artists, writers, business people included. The sunset celebration soon became a “tradition.”

Tennessee Williams initiated the ritual of applauding the sunset with a gin and tonic in hand.

The site of the present day Pier House was nearby. David Wolkowsky began construction of the initial Pier House Motel in the mid 1960’s. The physical features of the area comparable to Mallory Square at the time.

The sunset celebration grew. Not rapidly. It took time and more residents to discover the beauty of it all.  Mallory Square became the place to be at sunset during the early 1970’s. The crowd had grown, yet still small. Some nights as many as 40-50 people. Some evenings, less.

Gays were beginning to discover Key West and Mallory Square. The affluent of Key West, also. And street people and hippies. For tourists and residents, gays and straights, street people and the well heeled, and hippies, Mallory Square was the place to be at sunset.

What Brumgart had begin in the 1950’s had begun to bloom.

Minimal improvements had been made to the area in the 1960’s. Remaining in the 1970’s were the old docks, rotted dock boards, cracked sidewalks, and pot holes.

Throughout the 1970’s, entertainers preformed nightly. Jugglers, musicians, the Iguana Man (who walked around with 3 lizards on his shoulders), and others who “spontaneously” performed.

The crowds became bigger.  Hippies became a significant number. A few homeless, also.

By day and night, Mallory Square became home to the hippies. Their sleeping quarters at night included. Their attire ratty. Though of a nature acceptable today as being well dressed. Jeans and shorts with holes in them. Bandannas wrapped around their heads. Sandals.

They were into drugs. Hallucinogenic and regular such as marijuana. Some locals were upset with the drugs. Something I find amusing as the 1970’s were the hey day for drugs in Key West. Both for introduction into the U.S. and use locally.

The drugs were not the only concern for certain locals. The hippies were dirty, unkept, etc. Laid around smoking pot. Enjoying sex occasionally.

Certain locals wanted them out of Mallory Square and Key West in general.

City Commissioner Mary Lee Graham complained hippies and street people had found their way to Key West. They were “unwelcome newcomers” who had become regulars at Mallory Square. She was especially upset that they panhandled and slept on the streets as well as Mallory Square.

The Chairman of the Mallory Square Advisory Committee said he would never visit Mallory Square late at night. A person never knew what would happen with the hippies around.

In January 1973, 2 of the most prestigious groups in Key  West called for a “ban on hippies.” The Key West Woman’s Club and the Key West Garden Club. Mostly women at the time, the 2 organizations claimed hippies were responsible for the increase in crime and the decision of many downtown merchants to close early.

The Chamber of Commerce was anti-hippies also. The Chamber “refused” to be “identified” with the celebration. They refused to tell tourists about the sunsets at Mallory Square.

Joe Pinder was a banker and influential member of the Key West business establishment. He called the hippies “vagrants.” Wanted them arrested and sent to jail.

Some hippies were thrown in jail. Only for a few hours. For violating a local law that banned 2 or more musicians from performing in Key West without a permit. An improper charge in most instances. Those arrested were not musicians.

Not everyone agreed with those opposing hippies. There was a different perspective. Those persons expressed themselves publicly as did the anti-hippie group.

The Old Town Civic Association had been formed to foster an environment where tourists could feel safe. Its Director spoke of the “longhairs.” He argued they were not to be blamed for indecent exposure, panhandling, and profanity in the Mallory Square area.

City Manager Ron Stack said, “You can’t stereotype the elements that break our laws and commit crime. Our records show arrests of local citizens, transients, and the military. It’s unjust to single out any particular group.”

The Key West Citizen surveyed downtown businesses. None cited the presence of hippies as the reason they closed early.

An editorial disagreed with the “serious minded Chamber of Commerce members.” Urged them and Key West citizenry to visit Mallory Square for the sunset celebrations: “In none of the glories of the universe is this eternal display of brilliant color and fabulous design, is the mad wonder of the wild collection of our hippie community who make sunsets at the Mallory Docks a ritual experience.”

A primary reason the Chamber of Commerce and certain other entities were opposed to hippies is they brought no “disposable income” with them. They would not be spending money as they had no money.

Enjoy your Sunday!






    • Well… the spaces were deleted. It was supposed to look something like this:

      ………………. @…|…@
      ……………..ROCK – N – ROLL
      Kokomo Man

  1. I stayed at the Southernmost Motel in the 70’s. I was on the little beach under the motel and a hippy was standing in the water with a mask and snorkel. I asked him if that was a good place to snorkel. He told me that he was snorkeling all around the island and asked me if I wanted to join him. I declined. He was Pritam Singh. Geez, maybe I could have been somebody.

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