William Traphagen opened a tavern at this crossroads in 1704, in a Hudson Valley settlement then called Ryn Beck. His grandson Arent relocated the business to its current spot in 1766, where the King’s Highway met the old Sepasco Trail, and it took the name Beekman Arms after Judge Henry Beekman, one of the area’s original British landholders.
The Fourth Regiment of the Continental Army drilled on its front lawn in 1775, and George Washington, Alexander Hamilton, and Aaron Burr all passed through its doors during the Revolutionary era, a claim that gives it a case for being the oldest continuously operating inn in the country. The Delamater Inn next door, added to the property later, was designed in 1844 by Alexander Jackson Davis, one of America’s first professional architects, in the ornate Carpenter Gothic style. Owner Tracy Dows added the ballroom in 1918. The inn has been a Historic Hotels of America member since 2006.