King Street
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Description
The first version of a road/railline from Tocoi Landing to St. Augustine was built in 1859 by Dr. John Westcott. It was upgraded in 1860, but damaged during the Civil Ware. Repairs were made in 1866. Before the 1860s, a regular bridge was built over the San Sebastian River to connect with King Street to create another east-west entry point to St. Augustine (the older one being the Picolata Road/SR-16).
In 1871, the St. John's Railroad under the auspicious of William Astor began operations, but as a mule-drawn streetcar before being upgraded to locomotives. This was in time for President U.S. Grant's visit in 1879, but the depot was on the west side of the San Sebastian and eyewitness accounts of his visit indicate he came into town on a new bridge in a carriage, down tree-lined King Street. Henry Flagler purchased the railline in 1888.
After filling in Maria Sanchez Lake to widen the street and build his hotels, Henry Flagler described King Street as a “broad handsome thoroughfare” that linked the downtown of St. Augustine to St. Augustine’s newer west side and later extended the connection all the way to Anastasia Island. During the construction of the Ponce de Leon Hotel from 1885-1887, American architects Carrere and Hastings decided to widen the once narrow King Street to account for the increased traffic between the Ponce de Leon and Alcazar.
Following the construction of the hotels, existing concerns about health increased, due to waste and the disease-breeding sandy streets prompted action by Henry Flagler himself to improve King Street. In 1886, King Street became the first street in St. Augustine to have a sewer line when Henry Flagler and other property owners installed a twelve-inch sewer pipe at their own personal expense. Henry Flagler continued to improve the health and appearance of King Street by asphalting the section of King Street in front of the Ponce de Leon Hotel, hoping the city would follow this example and pave the rest of St. Augustine’s streets, but the city could not afford more than chords of wood starting in 1889.
Between 1886 and 1890, Flagler convinced his friend, Dr. Andrew Anderson to part with the front of his property along King Street so that Flagler could widen the street from the Hotel Ponce down to the railroad station. For several years, the trees Mrs. Anderson had planned years earlier along the front of the property were an island in the middle of the road. He also tried to have the name of the street changed to Alameda, but the City Council had agreed to change the names of Tolomato and Bronson and therefore refused to change another street name to please Flagler. In the 1895 Standard Guide though, King Street is called Alameda.
In 1895, a wooden bridge called the Matanzas River Bridge was built from King Street to Anastasia Island. Flagler did not want his new street marred by a trolley, but in 1906, a trolley line was installed down the center of King Street.
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Source
Map 1 (c.1770s): Reynolds, Charles B. The Standard Guide: St. Augustine, East Coast, Indian River and Lake Worth. St. Augustine, FL: C.B. Reynolds, 1895.
Map 2 (1884): Bloomfield, Max. Bloomfield’s Illustrated Historical Guide, Embracing an Account of the Antiquities of St. Augustine, Florida (with map). To Which is Added a Condensed Guide of the St. John’s, Ocklawaha, Halifax, and Indian Rivers. St. Augustine, FL: Max Bloomfield, 1884.
Photograph 1 (1870s): Van Campen, J.T. St. Augustine: Florida’ Colonial Capital. 3rd printing. St. Augustine, FL: St. Augustine Historical Society, 1971.
Photograph 2 (2025): Owens, Katherine. "Tocoi Landing Today." September 6, 2025.
Photograph 3 (1878): Tellier, Mark. St. Augustine’s Pictures of the Past: The Second Discovery. 1st edition. Published by the author, 1979.
Photograph 4 (1891): Biestadt, Edward. Sunlight Pictures: Saint Augustine. New York: The Artotype Publishing, 1891.
Photograph 5 (1906): Pollack, Deborah C. Felix F. de Crano: Forgotten Artist of the Flagler Colony. Lightner Museum, 2014.
Photograph 6 (1907): Bowen, Beth Rogero, and the St. Augustine Historical Society. St. Augustine in the Gilded Age. Acadia Publishing, 2008.
Photograph 7 (1940s): Bowen, Beth Rogero, and the St. Augustine Historical Society. St. Augustine in the 1930s and 1940s. Acadia Publishing, 2019.
Photograph 8 (2025): Zufelt, Holly. "Photograph of King Street." June 10, 2025.
The following books, articles, and/or websites were used to find information about this location:
Graham, Thomas. The Awakening of St. Augustine: The Anderson Family and the Oldest City, 1821-1924. St. Augustine, FL: Saint Augustine Historical Society, 1978.
Graham, Thomas. “Flagler’s Magnificent Hotel Ponce de Leon.” Florida Historical Quarterly 54 (July 1975).
Graham, Thomas. Mr. Flagler’s St. Augustine. Univ. of Florida Press, 2014.
Harvey, Karen. St. Augustine and St. Johns County: A Pictorial History. Virginia Beach, VA: The Donning Company, 1980.
Reynolds, Charles B. The Standard Guide: St. Augustine, East Coast, Indian River and Lake Worth. St. Augustine, FL: C.B. Reynolds, 1895.
Van Campen, J.T. St. Augustine: Florida’ Colonial Capital. 3rd printing. St. Augustine, FL: St. Augustine Historical Society, 1971.
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