New Tour Brings Saratoga’s Prohibition-Era Underworld to Life

SARATOGA SPRINGS — A new collaborative event will transport guests into one of the most fascinating and rebellious chapters of Saratoga Springs history. 

On Thursday, May 21, the Saratoga Springs History Museum will partner with the National Museum of Racing and Hall of Fame, Holiday Inn, Putnam Market, and Wishing Well Restaurant to present “Bridles & Bootleggers: When the Mob Owned the Spa City — The 2026 Trifecta Tour.” 

This one-night, multi-location experience will explore Saratoga’s 1920s era, a time when Prohibition laws were widely ignored, underground casinos flourished, and the worlds of Thoroughbred racing and organized crime collided. While much of the nation went dry, Saratoga remained vibrant with illegal liquor, high-stakes gambling, and behind-the-scenes deals that shaped the city’s identity. 

The Trifecta Tour guides attendees across three locations via a complimentary trolley. The evening begins at the National Museum of Racing and Hall of Fame, continues to the Holiday Inn, and includes a featured stop at the Saratoga Springs History Museum, before returning to the Racing Museum for the final portion of the program. 

At each stop, guests will hear from historians who bring this decade to life through site-specific storytelling. The experience also includes curated snacks and drinks. 

Tickets are now available, and space is limited. 

“This tour offers a unique opportunity to experience Saratoga’s history in the very places where it unfolded,” said James Parillo, director of the Saratoga Springs History Museum. “By combining storytelling, movement, and collaboration across institutions, we’re able to bring this remarkable era to life in a way that is both educational and unforgettable.”

For more information or to purchase tickets, visit www.saratogahistory.org.