Theodore Roosevelt’s Rough Riders Return to Oyster Bay

Image of the Rough Riders in Cuba during the Spanish American War from 1899. The Rough Riders were an American cavalry unit from 1898 that fought Spain in the Spanish American War.

A major historical reenactment of the Rough Riders is coming to Oyster Bay.  

This event, in partnership with the Town of Oyster Bay and Friends of Sagamore Hill, will take place on June 1, from 11 a.m. to 3 p.m. at Theodore Roosevelt Memorial Park. There will be reenactments consisting of performers from Boots and Saddles Productions and The Island Long Riders. The historical reenactment will highlight:  

  • Photo Opportunities with Generals Theodore Roosevelt and Joseph Wheeler re-enactors 
  • Rough Riders on Horses 
  • Shooting Demonstrations by the Island Long Riders 
  • Saber Performances by U.S. Cavalry Soldiers 
  • Historical Encampment with Canvas Period Tents 
  • Interpretive Performances and Live Music 

The Rough Riders was a nickname given to the 1st United States Volunteer Cavalry, one of three such regiments for the Spanish–American War and the only one to see combat. The U.S. had gone to war in opposition to Spanish colonial policies in Cuba, which was then torn by a rebellion. 1st United States Volunteer Cavalry Colonel Theodore Roosevelt, a strong advocate for the Cuban War of Independence, helped attract skilled horsemen eager to see combat to the regiment. Known as “Roosevelt’s Rough Riders,” they are best remembered for their conduct during the Battle of San Juan Hill. Several days after the Battle, the Spanish fleet sailed from Cuba, and in only a few weeks an armistice ending the fighting was signed. Despite the brevity of their service, the Rough Riders became legendary, thanks to Roosevelt’s writing his own history of the regiment and the silent film reenactments made years later. Colonel Roosevelt later became the 26th President of the United States of America. During his time in office, Roosevelt’s residence at Sagamore Hill in Oyster Bay became known as the “Summer White House” and the focus of international attention.

“We are so pleased to partner with the Friends of Sagamore Hill to welcome home our most famous resident, President Theodore Roosevelt, along with the Rough Riders,” said Town Clerk Richard LaMarca.

“What better way to celebrate the American spirit in advance of Independence Day than seeing history come alive as the Rough Riders and Theodore Roosevelt visit the place he called home, the hamlet of Oyster Bay,” said Town Supervisor Joseph Saladino. “This is a great opportunity for residents of all ages to step back in time and learn more about the Rough Riders, their skills and how they helped advance America’s profile around the globe.”