Located sixteen hundred feet above seawater and reached by steep and winding roads is Pawling’s Quaker Hill. Atop this hill but a short three miles east of the hustle and bustle of the Village, one can still find the same quiet serenity that attracted its first settlers in 1764. The meeting house of the Quaker Friends was built here 11 years before the Revolutionary War broke out. Parishioners would lay here in devout contemplation, alongside farmers eager to reap a harvest from the fertile plains of the valleys below, and patriots whose mission it was to secure the hopes of their generation and quell its fears.
The village was founded in 1788 and less than a century later, the New York and Harlem Railroad was extended into Pawling, bringing with it the prosperity and grandeur of the late 1800’s. The town would be home to two hotels that would accommodate the sudden influx of city dwellers yearning for the “clean air” of the countryside. The first, the Dutcher House - named after its founder, politician and railroad tycoon John B. Dutcher - would be located but a few footsteps away from the train depot located in the heart of the village. The second, also financed by Dutcher and backed by town notable Albert Akin, would be completed in June, 1881. Dutcher’s second project would boast 145 rooms and would command an extensive view of the rugged peaks of the Harlem Valley.
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.