The route begins north of the City of Poughkeepsie on the Hudson, winding into the town and past the remaining farms and orchards of LaGrange. Poughkeepsie was settled in 1687 after a patent was issued to Robert Sanders and Myndert Harmense. The city and town are governed separately.

CITY OF POUGHKEEPSIE measures 4.78 square miles. The first settlement, near the Falkill, retained its Wappinger Indian name, UPPUQUI-IPIS-ING, meaning “reed-covered lodge by the little water place.” Pronounced Poughkeepsie by Europeans, it became the Dutchess County seat in 1714. The courthouse built at the corner of Main and Market streets was the center of state government during the Revolutionary War years and was the scene on July 26, 1788, of New York’s ratification of the US Constitution. In 1799, the hamlet became a village and in 1854, a city. Boosters like Mayor Harvey Eastman (1871-74, 77, 78) made the city a civic and cultural center.

TOWN OF POUGHKEEPSIE encompasses 38.68 square miles and includes the centers of Arlington, Fairview, Rochdale, New Hamburg and part of the Village of Wappingers Falls. Major waterways are the Falkill, Casperkill, and Wappinger Creeks. Formed 1788, the town surrounds the city, extending into the Hudson. Early Dutch and English farmers settled near the river along the creeks, or “kills,” in Dutch. Proximity to the river and the King’s Highway soon made it the county center of commerce, government and transportation. It is the hometown of Governor George Clinton and painter/inventor Samuel F.B. Morse.

LAGRANGE spreading over 40.8 square miles, features the principle centers of Billings, LaGrangeville, Titusville, Arthursburg, and Freedom Plains. Its main waterways are the Sprout Creek and Wappinger Creek. Originally part of the Rombout and Beekman patents, during the American Revolution, this area saw Burgoyne’s defeated troops march through here on the way from Massachusetts to Virginia. Called “Freedom” when formed as a town in 1821, patriotic enthusiasts renamed it LaGrange in 1829 for LaFayette’s farm in France. Former dairy farms and orchards now sprout suburbs.