Monday, July 14, 2025
The Town of Oyster Bay, in partnership with the Friends of Sagamore Hill and Theodore Roosevelt Association, has announced that the Theodore Roosevelt Celebration will take place on May 31 and June 1 as the Rough Riders return to Oyster Bay, along with real life descendants for a reunion and symposium. This free, family-friendly weekend will take place at both Theodore Roosevelt Memorial Park and at Town Hall North in Oyster Bay.
“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.”
On May 31 from 11 a.m. to 3 p.m., Boots and Saddles Productions and the Island Long Riders will perform the following at Theodore Roosevelt Memorial Park:
Photo opportunities with Generals Theodore Roosevelt and Joseph Wheeler reenactors
Rough Riders on horses
Living history camp with campfire cooking demonstrations
Cavalry saber performances and mounted shooting show
Gilded Age historic carriage display
Historical tintype photography presentation by Bodor Tintype Studio
On June 1 from 11 a.m. to 3 p.m., a symposium will take place at Town Hall, located at 54 Audrey Avenue, Oyster Bay, for History Buffs. The first Rough Rider Reunion since 1968, descendants from the 1st U.S.V. Cavalry and Spanish American War will gather to participate in discussions with:
Jeff Heatley – a preeminent historian on the Rough Riders and author of “Bully: Colonel Theodore Roosevelt, The Rough Riders, and Camp Wikoff.”
Seth Isaacson – a leading firearms historian from Rock Island Auctions and contestant on a History Channel show featuring all the historical firearms of the Rough Riders and Spanish American War.
Pat Falci – an actor and historian from the 1997 Movie “The Rough Riders.”
Sue Sarna – Head Curator of the New Theodore Roosevelt Presidential Library in Medora, North Dakota, and longtime Sagamore Hill head curator.
Clay Risen – New York Times journalist and author of “The Crowded Hour” discussing Theodore Roosevelt, the Rough Riders, and the Dawn of the American Century.
“We are so pleased to partner with the Friends of Sagamore Hill and Theodore Roosevelt Association to welcome home our most famous resident, President Theodore Roosevelt, along with the Rough Riders,” said Town Clerk Rich 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 the Battle of San Juan Hill. For more information visit OysterBayTown.com/roughridersreunion.
