Oyster Bay Historical “Rough Riders” Reenactment

By Priya Persaud

Theodore Roosevelt and the "Rough Riders" will be saddling-up for one more ride through Oyster Bay.

In commemoration of the 125th Anniversary of Theodore Roosevelt’s 1st U.S. Volunteer Cavalry’s formation, the Oyster Bay Town Board and Town Supervisor Joseph Saladino are partnering with the Friends of Sagamore Hill to host a historical re-enactment of the monumental event.

“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,” stated 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.”

The re-enactment will feature performances by the Boots and Saddles Productions and the Island Long Riders.

The Rough Riders were a volunteer unit of the United States Army that played an important role in the 1898 Spanish-American War. They are best remembered for their conduct during the Battle of San Juan Hill in Cuba, where they overwhelmed the Spanish troops and provided a victory to the United States and the Cuban revolutionaries whom the US was helping to achieve the independence of Cuba.

The Rough Riders were commanded by Colonel Leonard Wood, whose second-in-command was Theodore Roosevelt who had just resigned as Assistant Secretary of the Navy. Their achievements in Cuba became legendary, and contributed to Roosevelt becoming President just four years later.

Next weekend, there will also be a Theodore Roosevelt Reprisor, Rough Riders on horses, saber performances by U.S. Cavalry Soldiers, and a mounted cowboy shooting by the Island Long Riders.

The historical commemoration will take place at the Theodore Roosevelt Memorial Park in Oyster Bay on Saturday, June 3rd, 2023 from 11 a.m. to 4 p.m.