May 24, 2026 · Updated May 24, 2026
The Long Island History Hunt launched Saturday from Oyster Bay, sending families to 26 Revolutionary War sites between Brooklyn and Montauk through September 30. The Oyster Bay-organized scavenger hunt offers a $1,776 grand prize and is timed to America's 250th anniversary, with all 26 locations tied to the region's colonial and Revolutionary War past.
The Long Island History Hunt launched Saturday from Oyster Bay, sending families and history enthusiasts across 26 Revolutionary War sites between Brooklyn and Montauk for a chance at a $1,776 cash prize.
The 2026 edition, titled "Redcoats and Rebels," runs through September 30 and doubles the number of locations from prior years. The program is organized by the Town of Oyster Bay and timed to America's 250th anniversary, inviting participants to spend the summer following the trail of the Revolution's Long Island chapter one site at a time.
Town Supervisor Joseph Saladino announced the start of the hunt on May 12 at Raynham Hall Museum in Oyster Bay, a house at 20 West Main St. that served as a British headquarters during the occupation and later as a node in the spy network that passed intelligence to General George Washington. The museum is one of the 26 designated stops.
Registration and selfie uploads are handled at LIhistoryhunt.com. Visitors photograph themselves at each site, upload the image to the platform, and complete a brief challenge. The prize structure scales with effort: completing any single site enters participants in a small-prize drawing; completing 10 or more qualifies for a $250 cash prize; completing all 26 earns the title "Revolutionary Trailblazer" and entry in the $1,776 grand prize drawing, with winners invited to a ceremony this fall.
Oyster Bay village served as a British garrison town from 1776 through 1783, one of the longest occupations of any American community during the war. Raynham Hall, home of the Townsend family, stands at the center of that history. Robert Townsend, whose family owned the house, became one of Washington's most productive intelligence sources as a member of the Culper Ring, passing information from occupied Long Island across the Sound to Connecticut and eventually to Washington's headquarters. The house at 20 West Main St. is open for tours with interpretive exhibits that put the spy operation in context before you head to the other sites.
Oyster Bay Harbor, a few blocks from Raynham Hall, was a British naval anchorage throughout the occupation. The geography that made it useful in 1778 is unchanged: a sheltered deep-water inlet with access to both the Sound and the open Atlantic. Walking from the museum to the waterfront takes about five minutes.
The 26 sites span Nassau and Suffolk counties and reach into Brooklyn and Queens. Most stops are accessible by car; Brooklyn and Queens sites are reachable by subway.
For a manageable first outing, start at Raynham Hall in Oyster Bay, then move east along the North Shore toward Setauket, where the Culper Ring's Long Island operations were centered. Several sites in that corridor are within 30 minutes of each other and can be covered in a half-day. The eastern concentration of sites in the Hamptons and on the Forks is better suited to a full day or a weekend, as British troops were billeted throughout Southampton and East Hampton and several of those structures still stand as house museums.
Most American history curricula treat Long Island as peripheral to the Revolution. The battle that gave British forces control of the island lasted one day in August 1776. What followed, seven years of occupation during which residents were taxed, quartered, and surveilled, receives far less attention.
The History Hunt is built around the argument that Long Island's role was not passive. The Culper Ring, operating out of Setauket and New York City, was one of the most effective intelligence operations of the war. Information the Ring provided helped Washington avoid strategic errors and contributed to the French alliance that eventually forced British surrender at Yorktown. That network ran through the same roads and harbors that Long Island residents use today.
Raynham Hall is the hunt's emotional center because the Townsend story is personal. Robert Townsend lived a double life for years, socializing with British officers in New York City while passing their conversations to Washington's handlers. His father received British officers in the family home in Oyster Bay. The tension of that arrangement sits in the actual rooms of the house on West Main Street.
Call ahead to small house museums before visiting. Many operate on limited hours or require advance registration, especially on weekdays. Outdoor monuments are accessible any time. Children who complete five or more sites receive special recognition from the program. Each site's challenge includes a brief historical summary written for general audiences, so no prior knowledge of the Revolution is required.
Individual site admission fees apply where they exist. Some museums offer discounts to History Hunt participants. The hunt runs through September 30 with no minimum pace requirement. Registration and the full site map are free at LIhistoryhunt.com.
