The Bull Moose in the Oldest City


The Bull Moose in the Oldest City 4To this day, Theodore Roosevelt remains one of the more popular and captivating U.S. presidents, due to his larger-than-life personality, frontiersman’s attitude, and role in conservation efforts across the United States. What is lesser known is that the twenty-sixth president visited St. Augustine not once, but twice. En-route to Cuba with the Rough-Riders to fight in the Spanish-American War, Roosevelt briefly camped on the green of Fort Marion (the Castillo de San Marcos). He would return several years later as President of the United States while touring around the South in the fall of 1905.

This visit was thanks to the efforts of the St. Augustine Board of Trade to generate more publicity about the town. Prior to his arrival, President Roosevelt previously stopped in Jacksonville to make a speech in mid-October of 1905. He arrived in the Oldest City on Saturday, October 21, where he stayed at Henry Flagler’s Hotel Ponce de Leon until the evening of Sunday, October 22. Due to fears of assassination attempts, his train to St. Augustine was heavily guarded, its route patrolled by military and local law enforcement personnel while Roosevelt was aboard.

To prepare for the arrival of the president and his guests, the Hotel Ponce de Leon was actually opened earlier than usual. When the president’s train finally arrived in St. Augustine, Theodore Roosevelt was greeted by an entourage of Florida East Coast Railroad officials and prominent St. Augustinians. The train station was vividly decorated with tropical flora, much of which had been shipped up to St. Augustine from West Palm Beach. After brief greetings and a walk to his awaiting carriage, Roosevelt headed into the Oldest City. This entourage was escorted by a posse of mounted military officers to the Ponce as citizens cheered, waved, and followed the procession.

Briefly, the convoy stopped at the city gate, where Roosevelt was presented a key to the city by Edna Perry, daughter of Sheriff Joe Perry. According to William R. Kenan, Jr.’s book Incidents By The Way- More Recollections (Second Edition), the party then continued on to the Ponce, entering the hotel from the main gate on King Street. As they exited the carriages, the group stepped into the courtyard, which had been lavishly illuminated with electric lights. A reception was briefly held in the Ponce’s rotunda, before the president resigned to Henry Flagler’s private suite in the hotel’s west wing, overlooking the courtyard. President Roosevelt remained at the Ponce until 7:00 that evening, when he departed for Fort Marion to give a speech.


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His route to the fort was again beautifully decorated, and special gas lines were constructed for the occasion to provide lighting at the fort, the first time such a feat had been accomplished at the Castillo. President Roosevelt spoke from the stairway leading to the terreplein, giving a speech in his usual style: a strong oratory praising courage, strength, morality, and the will of the people. Thousands gathered to hear and see him speak, surrounding the fort and crowding the bay with boats. Following the speech, Roosevelt went to the Hotel Valencia on St. George Street for a “Marine Supper.” Here he was joined by notable men from the city, county, and state, as the affair was strictly men-only. Once dinner concluded, Roosevelt returned to the Hotel Ponce de Leon around 11:00 PM.


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Sunday morning, he attended service at the Memorial Presbyterian Church, occupying the pew typically occupied by Henry Flagler himself. The Bull Moose reportedly sang heartily along with the hymns played that morning. After indulging in lunch, the president then took an unscheduled drive around the town to wave and speak with local citizens, before requesting a trip to North Beach. Boarding a vessel called the “Hustler” at the yacht pier, the president, some of his staff, and a group of locals went to North Beach Point for a swim. Roosevelt himself swam for nearly an hour in the chilly October water, and rumor has it that he swam in the nude. After this excursion and upon returning to the town, another large parade was held, in which the president traversed the city to another massive turnout of citizens eager to get to see Roosevelt in the flesh. Following the parade, he returned to the Hotel Ponce de Leon, where he remained until his departure at 9:00 that evening. Boarding his train to head north once again, Roosevelt was seen off by nearly 2,000 St. Augustinians.


Written by Robert Covert



“In 1905, ‘Teddy’ Roosevelt was Here,” The St. Augustine Picture. Published March 19, 1961.

“The President’s Visit to the ‘Oldest City,’ The Tatler, Vol. XV #1. Published January 6, 1906.

Untitled Article, The New York Times. Published October 22, 1905.

Incidents By The Way- More Recollections (Second Edition) by William R. Kenan, Jr. Published in 1949.