Theodore Roosevelt’s Rough Riders Return to Oyster Bay

Theodore Roosevelt’s Rough Riders Return to Oyster Bay

Town Supervisor Joseph Saladino and the Town Board, in partnership with the Friends of Sagamore Hill, announce a major historical re-enactment will take place on Saturday, June 1 from 11am to 3pm as Theodore Roosevelt and the Rough Riders return to Oyster Bay. This free family-fun event will take place at Theodore Roosevelt Memorial Park.


“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 Supervisor 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.”


Performed by Boots and Saddles Productions and the Island Long Riders, this historical commemoration features:


  • Photo Opportunities with Generals Theodore Roosevelt and Joseph Wheeler reenactors
  • 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


“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 LaMarca. “Join us for this free family-fun day in Oyster Bay.”


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.