The story
Take a deep breath and let the salt air of the Matanzas Bay settle around you. As you stand along Avenida Menendez, with the gray stone seawall at your side and the gentle, rhythmic lap of the tides in your ears, look toward the elegant structure at number 146. This is the Bayfront Westcott House, a stunning example of Mediterranean Revival architecture that has watched over this bay since 1914.
With its smooth stucco walls, symmetrical charm, and those iconic red-tiled roofs, it looks like a piece of the Spanish coast transported directly to the oldest city in America. It was originally built for Dr. John Westcott, a man of significant local influence who helped develop the Intracoastal Waterway.
But the house’s most tantalizing secrets aren’t found in medical journals or city blueprints. They are found in the shadows of the 1920s, during the height of Prohibition. At that time, while the rest of the country was officially dry by law, St.
Augustine was anything but. Its miles of jagged coastline, hidden inlets, and deep-water access made it a primary playground for rumrunners bringing spirits up from the Caribbean and the Bahamas. The local legend tells us that the proprietress of this very house was more than just a host to weary travelers; she was a vital link in an illicit chain of commerce.
On nights when the moon was thin and the federal agents were on the prowl, she is said to have climbed to the highest point of the roof, accessible through a small attic window. There, silhouetted against the dark Florida sky and the stars, she would swing a lantern in a steady, rhythmic arc. To a casual observer on the street, it might have looked like someone merely checking the shingles or perhaps a trick of the light.
But to the men on the boats out there in the dark, choppy waters of the Matanzas, that swinging light was a sophisticated language. A certain pattern meant the coast was clear to bring the "hooch" ashore. Another pattern warned that the law was waiting on the docks, and the sailors should turn back into the safety of the Atlantic.
Imagine her standing there on that red tile, the sea breeze whipping her hair, looking out past where the Bridge of Lions now stands, searching for a return signal from the inlet. She was a silent guardian of the city’s underground economy. Today, as you look up at those same rooflines, the house feels serene and stately, a beloved bed and breakfast where the only things being served are gourmet meals and warm hospitality.
But as the sun sets over the bay and the shadows stretch across the water, it is easy to imagine a flickering golden light once again cutting through the mist, signaling a boat full of forbidden treasure to finally come home to St. Augustine. Take a moment to appreciate the quiet dignity of the Westcott House, a place where history isn't just about what is written in the books, but about the secrets we chose to keep.