The Rough Riders gallop into Oyster Bay

For the second year in a row Oyster Bay was transported back to the early 1900’s on June 1, as the community gathered for a major historical reenactment of Theodore Roosevelt and the Rough Riders. Organized by the Town of Oyster Bay in collaboration with the Friends of Sagamore Hill, the event offered an immersive experience, attracting families, history enthusiasts, and curious visitors to watch the president’s fabled cavalry unit perform acts of derring-do and learn about history.

“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,” Joseph Saladino, town supervisor, said in a statement.

The reenactment, performed by Boots and Saddles Productions and the Island Long Riders, featured various engaging activities and displays. Attendees enjoyed photo opportunities with reenactors portraying Generals Theodore Roosevelt and Joseph Wheeler, watched Rough Riders on horseback, and witnessed shooting demonstrations and saber performances by U.S. Cavalry soldiers. The event also included a historical encampment with canvas period tents, interpretive performances, and live music.

“It’s important for the youth of our community to understand where they live, and what happened here,” said Town Clerk Rich LaMarca. “You don’t want to ever forget what went on in the past and how lucky we are to have the freedoms that we have because of people like the Rough Riders.”

The Rough Riders, formally known as the 1st United States Volunteer Cavalry, were famed for their role in the Spanish American War. Under the command of Colonel Theodore Roosevelt, they became legendary for their bravery during the Battle of San Juan Hill, helping to secure a decisive victory that boosted America’s global profile. This reenactment aimed to educate the public about their storied past and Roosevelt’s profound impact on American history.

“We had families from as far as Northport, Suffolk and even families from Connecticut,” Walsh said. “So not only do we teach our own residents about Theodore Roosevelt, but we got to teach visitors about him too.”

Among the highlights were the antique tools and a Victor phonograph, which captivated younger visitors, and an original stagecoach carriage, where children could sit and imagine life in Roosevelt’s era. Food demonstrations featuring cast iron pots and traditional cornmeal preparation added to the authentic historical atmosphere.