The second hotel, set high atop Quaker Hill, would be named by Admiral John Lorimer Worden, the former commander of the Civil War ship USS Monitor. Struck one day by the sweeping landscape of rolling peaks and valleys below, Worden chose the nautical term, “mizzen,” used in sailing to describe the sail, mast, and platform located toward the stern of the ship, to describe the hotel’s spectacular location. It would be called, he decided, the Mizzen-Top Hotel.
The din of the financial crisis of the Great Depression, however, loomed overhead. In 1906, Dutcher would sell the Dutcher House to Dr. Frederick L. Gamage, headmaster of St. Paul’s School of Long Island, who eagerly sought a location for an institution of his own. The Dutcher House would thus be transformed into the Pawling School, the first location of the all-boys preparatory school that is now known as Trinity-Pawling. With conditions becoming ever more dire, Mizzen-Top would soon be demolished, its name a monument to the courage and endurance of that trying time.