Teddy Roosevelt and the Rough Riders in Tampa, 1898

Roosevelt and the Rough Riders came to Tampa in late May 1898 because the War Department had made Tampa the official port of embarkation for the Army bound for Cuba in the Spanish American War.

President McKinley declared war on Spain on April 25, 1898, and the government picked Tampa for its location, its deep water port and its link to Henry B. Plant, whose railroad, steamships, lobbying and War Department connections and big Tampa Bay Hotel all served the Army (National Park Service). Hillsborough County calls itself the primary staging area for soldiers bound for the war (Hillsborough County).

The Rough Riders were the First U.S. Volunteer Cavalry. Roosevelt resigned as Assistant Secretary of the Navy in May 1898 to join it, and he and the regiment's commander, Colonel Leonard Wood, trained the men at a camp in San Antonio, Texas, before they went to Tampa at the end of May (Library of Congress). The sources differ on his rank: the Army history calls him Lt. Col. Theodore Roosevelt when he reached Tampa (U.S. Army Transportation Corps), while the National Park Service and Hillsborough County both call him Colonel Roosevelt at the time.

Tampa was small for the job. The Army history describes a town of about 10,000 people whose main industry was cigar making, with gravel and planked roads, a handful of general stores and one telegraph office (Army Transportation Corps). Over 30,000 troops passed through Hillsborough County in 1898 (Hillsborough County marker).

The Tampa Bay Hotel, on the west bank of the Hillsborough River (Hillsborough County), was Army headquarters in 1898, and Roosevelt talked strategy with generals in its Writing and Reading room while the Rough Riders drilled on horseback on the hotel grounds.

The Army set up seven camps around Tampa and made Plant's hotel the headquarters for the officers planning the campaign and waiting for orders to sail (National Park Service). A train ran right up to the hotel's west side, so troops, officers and officials came and went all day. Clara Barton, founder of the American Red Cross, also came to the hotel to organize hospital facilities.

The wait gave the episode a nickname. Officers sat in rocking chairs on the Tampa Bay Hotel veranda talking strategy and politics, and some locals called the conflict the Rocking Chair War (NPS). The Army history adds that general officers, newspaper correspondents and foreign observers from Great Britain, Germany, Russia, France and Japan milled about the hotel, as Roosevelt himself noted (Army Transportation Corps).

The Tampa Bay Hotel was new in 1898. Plant built it between 1888 and 1891 for over $2 million, 900 feet long and five stories high with over 500 rooms, on 150 acres of grounds (NPS). The Army history describes the hotel as resting on six acres; the two federal accounts disagree, and the NPS lists a golf course, a race track and a casino among the attractions on its 150 acres.

Very: Roosevelt called Tampa in 1898 a perfect welter of confusion, because no one received arriving regiments, there was no food for their first twenty four hours and every load had to move on one track to Port Tampa.

When Lt. Col. Roosevelt's train arrived, there was no central authority to receive the Rough Riders and no guidance on where to camp (U.S. Army Transportation Corps). Three to five regiments arrived in Tampa every day, and by 25 May the city held 17,000 troops, so General Shafter opened extra camps in Lakeland and Jacksonville.

The bottleneck was the railroad. Henry B. Plant owned the small one track railroad that ran nine miles from Tampa to the Port of Tampa, and the Army history says he refused to let other rail companies use it and even ran sightseeing trains so residents could watch the military (Army Transportation Corps). At the port, a 21 foot channel let large ships in and the wharf could dock thirteen vessels at once.

Black regiments shared the wait. Ten regiments, including two Black units, the Twenty fourth and Twenty fifth Infantry, camped on the fringes of the Tampa Heights neighborhood, and the Buffalo Soldiers later earned five Medals of Honor at San Juan and El Caney (Hillsborough County marker). Their marker stands at East Columbus Drive and North Central Avenue.

The Rough Riders reached Port Tampa by seizing an engine and coal cars after a six hour wait for a train, then took over the transport Yucatan and sailed with the fleet on June 13, 1898, without their horses.

Ordered to the station at midnight, the regiment waited six hours, then took an engine and some coal cars and backed down the track to Port Tampa; Colonel Charles Humphrey assigned them the Yucatan, a ship already promised to other units, and Roosevelt got his men aboard first and kept it (U.S. Army Transportation Corps). Space was short: the Cherokee, equipped for 570 men, carried 1,040, and Colonel Wood could take only two of his three cavalry squadrons and no horses from Port Tampa.

Most vessels had left the dock by 1400 on 8 June, then the fleet waited three more days; the War Department issued sailing orders on 12 June, and on 13 June the fleet steamed out of the bay for Cuba (Army Transportation Corps). The Library of Congress guide gives the same date, June 13, for the regiment's sailing for Santiago de Cuba (Library of Congress). Port Tampa Bay's own history still calls the port Teddy Roosevelt's launching point for the Roughriders (Port Tampa Bay).

Roosevelt's Tampa episode spans about two weeks, from the Rough Riders' arrival at the end of May 1898 to the fleet's departure from Tampa Bay on June 13, 1898.

Earlier versions of this Tampa page gave June 3 for the arrival and June 14 for the sailing; neither date appears in the Army or Library of Congress sources checked for this revision, which give the end of May and June 13, so the table follows them.

The Tampa Bay Hotel, now Plant Hall at the University of Tampa, is the main surviving 1898 site, and the Plant Museum in its south wing at 401 West Kennedy Boulevard posts hours for every day but Monday.

The hotel closed in 1932; Plant had died in 1899, his heirs sold the hotel and 50 acres to the City of Tampa in 1905, and in 1933 the city leased the building to the University of Tampa for 100 years at one dollar a year (National Park Service). The Writing and Reading room where Roosevelt met the generals can still be seen.

The museum gives its hours as Tuesday to Saturday 10 am to 5 pm and Sunday noon to 5 pm, closed Monday and on Gasparilla parade day, with the phone number 813.254.1891 (Henry B. Plant Museum). The weekly hours panel at the top of the same page showed Saturday as closed when it was checked on October 18, 2026, so a Saturday visit is worth confirming by phone first. It says the city opened the Tampa Municipal Museum in the hotel's south wing in 1933 and that the building, renamed Plant Hall, is a National Historic Landmark for its role as a military headquarters in the war.

For the camps, the Hillsborough County marker at East Columbus Drive and North Central Avenue in Tampa Heights marks where the 24th Infantry camped (Hillsborough County). Last verified: October 18, 2026, against the NPS Tampa Bay Hotel page, the Army Transportation Corps history and the Plant Museum's posted hours.