Rough Riders

American  

plural noun

1. the members of a volunteer regiment of cavalry organized by Theodore Roosevelt and Leonard Wood for service in the Spanish-American War.

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Rough Riders Cultural  

1. The nickname of a volunteer group of cavalry led by Colonel Theodore Roosevelt in the Spanish-American War. They were famous for a victorious charge at the Battle of San Juan Hill in Cuba.

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Example Sentences

The image of him and his Rough Riders charging up Cuba’s San Juan Hill became the Spanish-American War’s enduring image, but the orders he would give for operations in the Philippines would prove more consequential.

From The Wall Street Journal • Nov. 5, 2025

Hundreds of volunteers came to place flags before each grave on Saturday and reenact the Rough Riders of the Spanish-American War.

From Los Angeles Times • May 26, 2024

Downtown, you’ll find the historic Rough Riders Hotel, pince-nez-wearing teddy bears in the gift shops and, in front of the Old Town Hall Theater, a bronze statue of the man himself.

From New York Times • Oct. 27, 2023

I charged up San Juan Hill with the Rough Riders and joined the doughboys over there.

From Washington Times • Jul. 2, 2023

He told her that he was serving with Teddy Roosevelt and his Rough Riders.

From "Summer of the Monkeys" by Wilson Rawls