Make for the midway: 2019 guide to county fairs in the Hudson Valley

Racing pigs at the Ulster County Fair. (Photo by Will Dendis)

False, roving cities of the night: A good county fair should not want for a hint of menace, for a bit of the unsavory and the sense that the whole two-bit illusion serves as cover for those “wanted” elsewhere. They say that at Disney World, you never see a door marked “Staff Only,” nor a man carrying a mop and bucket with a walkie-talkie on his hip emerging from it. All sightlines are composed. At a good county fair, you catch those sordid peeks behind the flimsy illusion with a frequency that should be at least a little discomfiting.

And if families of motorcyclists flipping around inside an orbital cage while a sh*t-kicking country/rock band sings about the flag and what it’s gonna do to you, while somewhere a distorted audio loop keeps saying something about “the world’s biggest rat” as you stumble into what sure seems to be an authentic, unregulated knife-throwing exhibition, make you nervous, imagine now how many of your neighbors feel at O+. But county fairs are for everyone: everyone who dares believe in our commonality, our blood ties to livestock and the Earth and in the high ritualistic value of pure diversion and unhealthy fats as your great-grandparents enjoyed them.


The Orange County Fair in Middletown – so close to Alto Music that I can smell the guitars – kicks off the fair season locally between July 18 and 28. It features, among other bar-rising diversions, pig races and extreme jousting. My own childhood fair, the tidy Ulster County Fair, takes over the County Fairgrounds in New Paltz from July 30 through August 4, with live music each night including country/rock stars like Little Texas and rock royalty like Fran Cosmo, formerly of Boston.

The Grahamsville Fair in Neversink calls itself the “Little World’s Fair,” and claims to be, in its 140th year, the oldest independent fair in New York. I believe it, and I love the focus on the traditional, substantive fair fare: emphasis on livestock, agriculture, practical demonstrations and temperate fun as Carrie A. Nation envisaged it. It runs from August 16 through 18.

A cow at the Dutchess County Fair (photo by Dion Ogust)

Everyone knows that the Dutchess County Fair (August 20-25) is a different kind of animal, where the meats are grass-fed and the dunking-booth clown issues barbs as pointed as Rabelais (to whom he actually may be related). It’s a prim affair more attuned to the estates, mansions and boutique farms of northern Dutchess. But it is everyone’s fair, too, and the food simply cannot be beat.

Fair season flows north, and the Columbia County Fair in Chatham takes up the mantle from August 28 through September 2. Pumping up the volume that reminds us of our endangered freedoms, Columbia is big on the gas sports: demolition derby, monster tractors, truck-pulling.

The websites are as rustic as the fairgrounds themselves, and about as slick as the midways. But the early-’90s webcraft just adds to the charm, and all the info is there.

Orange County Fair
July 18–28

Ulster County Fair
July 30–August 4

Grahamsville Little World’s Fair
August 16-18

Dutchess County Fair
August 20–25

Columbia County Fair
August 28–September 2