The Dutchess County Fair is held annually in Rhinebeck, New York, usually during the last full week in August.

The Dutchess County Agricultural Society, formed in 1841, first organized the fair in 1842 at Washington Hollow in Pleasant Valley, New York.

[2] The fair initially alternated between Washington Hollow and Poughkeepsie before moving to Springbrook Park in Rhinebeck in 1919.

[3] The Society faced heavy debt in the Depression era after the cancellations of the 1927 and 1928 fairs due to flooding.

A financial upturn in the late 1940s allowed the Society to repay its debt and acquire the Springbrook Park land renaming it to the Dutchess County Fairgrounds.