The first of the three hamlets to make up the town of Pleasant Valley.
In 1737 Presbyterians from Connecticut came to this area and built a church named the Pittsbury Church 1747. It was at this church that a group of Torys wintered in 1777. While practicing marching they were surprised by a group of patriots, defeated and marched off to Sharon, Connecticut.
The church stood until 1859 at which time it was purchased by Methodists who tore it down and built the church building now standing on the site.
Henry Filkin, who was High Sheriff of Dutchess County, had the first road, which later became Dutchess Turnpike, named for him. Filkinstown Road was built in 1733. It was this road which led the settlers west.
Luther Gay was the first postmaster. He was appointed in 1826. The post office was discontinued in 1903.
The closest school, #11 was on Tinkertown Road. This school is shown on the 1867 Beers Atlas map of the town.
The first Dutchess County agriculture fair was held in Washington Hollow in 1819 and from then on until 1841 it shared honors with Poughkeepsie in hosting the fair but most were held here through 1888. The fair activity centered around Emigh’s Hotel which stood on the intersection between Route 44 and Route 82. It burned in the early 1940s and in the 1960s the property became a turkey farm. At present the site is headquarters for Troop K of the New York State Police.
The cemetery of the original church is across from the church building(s). Early stones show burial of Simon and Zachariah Flagler, a name familiar to us even now.