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Wood and Roosevelt, who was given the rank of Lieutenant Colonel, received an abundance of responses from eager young men from across the country. The difficulty was said not to be one of attracting volunteers, but of rejecting them. Various states offered entire, organized local militias, but Wood could draw volunteers from three states allotted to him and from what was then known as the Indian Territory. One of the first volunteers was Bucky O'Neill, the Mayor of Prescott, AZ and a famous frontier sheriff. He was commissioned Captain of Troop A. Captain Llewellen of New Mexico was one of the most famous peace-officers of the frontier, and Lieutenant Ballard was another former peace officer who had gained fame for breaking up the infamous Black Jack Gang. Benjamin Franklin Daniels, who had one ear partially bitten off in a fight, had been the Marshall of Dodge City and he joined the unit, as did the deputy marshal of Cripple Creek, Colorado, Sherman Bell.
Wood went to San Antonio to begin assembling the regiment, to be later joined by Roosevelt. Within days, additional men arrived from the Indian Territories, including some members of the Cherokee nation and several former Texas Rangers. Originally the unit was allotted 780 men, but the authorized number was raised to 1,000. This included some volunteers from Ivy League schools such as Harvard, Yale, and Princeton. Many of these were star athletes. Former Princeton football standout James Robb Church came to the Rough Riders and was appointed as the regiment's assistant surgeon.
Roosevelt addressed the task of outfitting the soldiers. Some were given hot, wool uniforms, useless for men expected to fight in a tropical climate. Roosevelt was able to outfit the Rough Riders in khaki. On Saturday April 30th, Roosevelt sent a message to Brooks Brothers of New York requesting, at his personal expense, a tailored lieutenant-colonel's uniform which he said he required "by next Saturday" (May 7). Brooks Brothers met the requested deadline. More important was the need for weapons. Many of the volunteers from the west came to the regiment with their own Winchesters which would fire the Government cartridge. Those who preferred these personal weapons were allowed to retain them. Officers were armed with pistols, but the men of the regiment were, at Colonel Wood's insistence and thanks in large part to Roosevelt's connections, outfitted with the new Krag-Jorgensen rifles which had the advantage of using smokeless powder.
On May 15th Roosevelt arrived in San Antonio to join Colonel Wood and meet his Rough Riders. He later wrote:
"They were a splendid set of men, these South westerners--tall and sinewy, with resolute, weather-beaten faces, and eyes that looked a man straight in the face without flinching. In all the world there could be no better material for soldiers than that afforded by these grim hunters of the mountains, these wild rough riders of the plains."
For two weeks Roosevelt worked training the Rough Riders while Colonel Wood finished the process of procuring the necessary saddles, arms, ammunition, and other material. As the month of May came to a close, the unit was sent to Tampa, Florida, to meet with other forces destined for Cuba. It was from Tampa that Major General William Shafter would transport his Fifth Army Corps to the shores of Cuba. On May 29th, the Rough Riders headed for the rail yard to begin what was then a four day trip to Tampa.
The regiment was broken up into seven sections for the trip to Tampa. Colonel Wood left first, taking three sections with him, while Roosevelt left later with the remaining four sections. In addition to 1,000 men and their horses, the regiment had 150 pack mules. The men were not permitted any personal luggage. Along the route the trains made periodic stops so that the horses could be tended. On these stops, people came to cheer on the soldiers. Roosevelt wrote:
"Everywhere the people came out to greet us and cheer us. They brought us flowers; they brought us watermelons and other fruits, and sometimes jugs and pails of milk--all of which we greatly appreciated."
The train tracks ended in Tampa where the men "disembarked in a perfect welter of confusion," according to Roosevelt. Approximately 30,000 American soldiers had arrived in Tampa by then, providing a logistical challenge. No one met the Rough Riders when they arrived or told them where they would be staying. The men stayed on the trains the first night. Wood, Roosevelt and the other officers purchased food for their men on their own nickel. The men continued their training in the nearby woods until their orders arrived.
The Rough Riders learned that they were to become part of General Shafter's Fifth Corps. The Cavalry soldiers resigned themselves to the news that their horses would have to be left behind. They would be going to war as a dismounted cavalry unit. Not all the Rough Riders were being sent. Only 560 would get their opportunity for action. "I saw more than one, both among the officers and privates, burst into tears when he found he could not go," Roosevelt wrote, adding "To the great bulk of them I think it will be a life-long sorrow."
On the evening of June 7, 1898, Colonel Wood and Lieutenant Colonel Roosevelt received their orders. At midnight their troops were to meet a train for the 9-mile trip from their camp to Port Tampa where at daybreak they would board their transport ships. But when the Rough Riders arrived at their appointed boarding site, the trains were no where to be found. At 3:00 A.M. the Rough Riders received orders to march to an entirely different track, which they promptly did. On arrival at this location once again there were no trains. At 6:00 A.M. a coal train moved down the track, coming from Port Tampa, heading in the opposite direction. Roosevelt and Wood halted the train, seized it, and ordered the engineer to transport the Rough Riders to Port Tampa. When they arrived at the port, Wood and Roosevelt realized that the transport ship, the Yucatan had also been assigned as transport for the Second Regular Infantry and for the 71st New York Volunteer Infantry. The ship was going to be packed.
Throughout the day, amid the continued confusion, 16,000 American soldiers and their equipment were loaded aboard the transport ships that would ferry them to the shores of Cuba. The Rough Riders were among the first to board, thanks to their commanders' tenacity.
On the morning of June 9th, a Naval officer had witnessed the presence of a large number of ships in the distance, and mistook them for Spanish vessels. The transport ships in Tampa were ordered to remain anchored while American warships went in search of the Spanish. For four days the soldiers aboard the anchored transports did their best to survive the hot sun and cramped quarters while the ships bobbed at anchor.
At last, on the evening of June 13th, the Yucatan hoisted anchor and joined the fleet in moving out for Cuba.