History of the Rough Riders Flag

The regimental flag for the first volunteer cavalry in the Spanish-American War, better known as the “Rough Riders”, is a colorful flag for a colorful group of characters. Under the leadership of Colonel Leonard Wood and second in command Theodore Roosevelt, the army unit included a diverse group of rough and tumble cowboys and miners, polished Ivy League athletes, New York City cops, Texas Rangers and Native Americans.

About the Rough Riders

A statue of President Theodore Roosevelt on horseback is displayed against the blue sky at the city park in Mandan ND. Before he was President of the United States, Theodore Roosevelt was the Assistant Secretary of the Navy. However, he resigned in May 1898 to organize the first voluntary cavalry in the Spanish-American War. The original plan for the unit was to recruit men from the Indian Territory, New Mexico, Arizona and Oklahoma, but when Roosevelt joined, he brought with him an eclectic mix of men from his many walks of life, including cowboys, miners, law enforcement officials and Native Americans. Newspapers nicknamed them the “Rough Riders”.

The U.S. was fighting over Spain’s colonial policies with Cuba, and the Rough Riders were the most publicized of all the units fighting on the island – often portrayed riding after the bad guys in a cloud of dust with slouch hats and handkerchiefs around their necks, like in an old Western movie. While the Rough Riders didn’t win the war on their own, they participated in the capture of Kettle Hill, and are perhaps best remembered for their charge up San Juan Ridge in the Battle of Santiago on July 1, 1898.

A few days after the seizure of San Juan Hill, the Spanish Fleet fled Cuba, and it was just a matter of weeks before the war ended, and the U.S. was victorious.

About the Rough Riders Flag

"Rough Riders" Teddy Roosevelt Flag

The regimental yellow silk flag of the Rough Riders was carried up San Juan Hill and planted firmly at the top, along with our country’s Stars and Stripes, upon successful capture of the ridge.

The flag itself features a bald eagle on a bright yellow field holding an olive branch and a bundle of arrows in its talons. In its beak, the eagle carries a ribbon with the traditional motto of the United States, “E pluribus unum”, or “Out of Many, One”. There are 13 stars above the eagle’s head and 13 stripes on the shield over its breast to represent the first 13 states. Below the eagle, a red scroll reads, “1st U.S. Regiment Volunteer Cavalry”.

A variation of the Rough Rider flag was also adopted as the official North Dakota state flag in 1911.

Both the Rough Rider flag and the North Dakota flag are available for purchase from Gettysburg Flag Works. For questions or custom orders, give us a call at 1-888-697-3524 or contact us online.

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