The atmosphere of Pleasant Valley has changed a great deal since the first settlement. Henry Hudson's record of his exploration of the river that was to bear his name recalls both his adventures and his misadventures, painting a vivid picture of the past.

The first settlement in the town of Pleasant Valley occurred prior to 1740, at "Pittsburgh", or Washington Hollow. 1740 brought the settlement of the village of Pleasant Valley. The Moravian mission- aries who arrived at the Mohican village of Shekemeko in 1740 must have had some influence on other Dutchess County settlements, for they certainly helped to make the environs safer here in Pleasant Valley.

The stone barn on the Niagara Mohawk Road in Pleasant Valley is very rare in this part of the state. It's similar to the barns built by German settlers in Pennsylvania, with slits on all four sides to provide light and ventilation. The exact date it was built remains a mystery even today. Half of the Rossway farmhouse was built around 1740.

In the fall of 1777, when it was feared that the British would storm Poughkeepsie, Governor Clinton sent his wife to Pleasant Valley to hide. It appeared that one of the safest places to be during the war was Pleasant Valley. Pleasant Valley had no doctors during the revolutionary times. In the last half of the 1700's the use of bricks for houses became wide spread.

In 1806 Pleasant Valley's great bridge had been replaced by a covered bridge. The first Dutchess County fair was in 1892. In the years 1861 to 1865, 148 men from Pleasant Valley went to the war and 15 never came back. In the winter of 1888 a blizzard forced a closing of the Dutchess Turnpike.