Dutchess County Fair - Where Don McLean Won A Talent Competition

In 1964, singer/songwriter Don McLean (“American Pie” among other hits) won the fair’s first talent competition.

According to reports, radio personality Raphael Mark arranged a performance for McLean at Dutchess Community College. Mark’s wife Frances was quoted in the Poughkeepsie Journal as saying, “This song is never going to make it. It’s too long”. Still, “American Pie” remains one of the biggest hits and Don McLean returned to Dutchess County Fair in later years as a headliner.

The Dutchess County Fair — by our calculation it ought to be the 175th Annual Fair — is an urban delight if only because it is so rural.

For example, there are over 1500 animals on display to the delight of children, and  goat-milking demonstrations to horse and dog shows. There are floral-design displays and tractor pulls. The faIr has displays of farming tools and competitions for best fruit and vegetables, best crop seed samples, and best homespun wool and flannel cloth. There’s even a Chicken Clucking & Rooster Crowing contest. In 2008, the baking contest featured a chicken-shaped cake.

And there’s the pig race. Watch:

One of the most crowd-pleasing early attractions was the plowing competition. Isaac Sands took home the top prize in 1846 by turning over a quarter-acre of soil in 28½ minutes.

The fair moved to its current Rhinebeck home in 1919. Dignitaries who have attended the fair include Presidents Theodore and Franklin Roosevelt, and NY Governors Thomas Dewey and Averill Harriman.

In 2020, the fair was cancelled owing to the pandemic. That was the  sixth time the fair had been cancelled. (In 1916 and 1918 (for money troubles), in 1927 and 1928 (heavy rains and flooding), in 1942 (World War II) and in 2011 (Hurricane Irene).

There cannot not be a mention of dairy of course. A Dutchess County Fair milkshakes is a delight with 13% butterfat. Lesser milkshakes have about half that much.

Here is a link to the Dutchess County Fair event page: