The Hudson Valley and Catskills region carries 15 of the 92 events in this directory, and its shape is unusual. The county fairs cluster tightly across late July and August, then a second wave of harvest, craft, and seasonal events arrives from late September through the middle of October.
Orange County alone accounts for four separate entries, in four different towns, spread across four months. That is the densest single-county cluster in the region.
Orange County: Four Dates, Four Towns
The Goshen Historic Track is the first Orange County date of the year, a single day on July 3 recorded as an agricultural event with animals and competitions.
Three weeks later the county's main event opens. The Orange County Fair in Middletown runs July 23 to August 2, eleven days with animals, competitions, and a ride midway. The Orange County 4-H Youth Fair in Otisville sits inside that window, July 24 to 26, and its record lists animals, competitions, and kids activities with no rides, so it reads as an exhibition and showing event rather than a second midway.
The county's fourth entry lands in autumn. Warwick Valley Applefest is a one-day festival on Sunday, October 4, established in 1989, tagged food festival, craft, and family.
Late July: Three More Fairs in One Week
The Greene County Youth Fair in Cairo runs July 23 to 26, exactly the same four days as the Orange County 4-H fair, so those two are an either-or rather than a pairing.
Putnam County Fair and 4-H Showcase in Carmel is the shortest of the group, July 25 to 26, and one of only two agricultural entries in the entire directory recorded with free admission. For a family testing whether a county fair lands with young children, a free two-day 4-H showcase is the low-risk version.
August: Ulster, Sullivan, Delaware, Dutchess
The Ulster County Fair in New Paltz opens the month, August 4 to 9, with a ride midway on its record. The Grahamsville Little World's Fair in Sullivan County takes three days, August 14 to 16, one of two fairs in New York carrying that traditional name.
The Delaware County Fair in Walton follows August 17 to 22, and The Dutchess County Fair in Rhinebeck closes the month, August 25 to 30. Four fairs, four consecutive weeks, no overlap between them. It is the cleanest stretch of the regional calendar.
Rhinebeck Twice in One Year
Rhinebeck is the only town in the region with two entries, and they sit at opposite ends of the season. The Dutchess County Fair takes the last week of August. New York State Sheep & Wool Festival returns to the same town October 15 to 18, a four-day event tagged agricultural, craft, and artisan, with animals, competitions, and crafts on its record.
If you want one town and two genuinely different days out, that is the pairing to build a year around.
Labor Day, Then the Harvest Run
The Columbia County Fair in Chatham is the region's Labor Day fair, September 2 to 7, running the same six days as the Fonda and Schaghticoke fairs to the north.
Late September turns to food. Hudson Valley Garlic Festival takes September 26 to 27 in Saugerties, Ulster County, with crafts, food, and live music. It shares that weekend with the Naples Grape Festival in the Finger Lakes, which is a real conflict if you were planning to do both.
Westchester: One Night of Music, Seven Weeks of Pumpkins
Hudson River Music Festival is a single day in Croton-on-Hudson, June 21, and the only entry in this region tagged music and nothing else.
The same town hosts The Great Jack O'Lantern Blaze, which opens September 18 and runs to November 8. That is the longest autumn window in the directory and the last event date we carry for the whole 2026 season.
Planning Notes
The dates above are windows, not schedules. A six-day county fair does something different on each of those days, and the directory records the range rather than the programme.
County fair dates shift year to year because most are pinned to a weekday pattern rather than a calendar number. Confirm with the fair itself before you commit to travel or lodging.
