Of the 15 events in the Hudson Valley and Catskills on the 2026 calendar, four are in Orange County, in four different towns: Goshen, Middletown, Otisville, and Warwick. No other county has more than two.
County fairs filled late July and August, and a second group of harvest, craft, and seasonal events spans late September through the middle of October.
Orange County: July 3 to October 4
The Goshen Historic Track, listed as a National Historic Landmark harness racing venue, had the first Orange County date of 2026, July 3 (that date was not confirmed).
The Orange County Fair in Middletown ran eleven days, July 23 to August 2, with a ride midway. The Orange County 4-H Youth Fair in Otisville, organized by Cornell Cooperative Extension at the 4-H Park, fell inside that window on an unconfirmed July 24 to 26. It was a youth exhibition fair, and no ride midway was listed for it.
Warwick Valley Applefest was a one-day festival in downtown Warwick on Sunday, October 4, from 9am to 5pm. It was established in 1989, and the organizers listed more than 150 craft vendors, more than 75 food vendors, and four live music stages.
Late July: Greene and Putnam counties
The Greene County Youth Fair in Cairo was listed for July 23 to 26, a date that was not confirmed. Its listed dates covered all three days of the Orange County 4-H fair.
Putnam County Fair and 4-H Showcase in Carmel was listed for July 25 to 26 (that date was not confirmed). The fair's venue was Putnam County Veterans Memorial Park, and admission and parking were both free.
August: Ulster, Sullivan, Delaware, Dutchess
The Ulster County Fair in New Paltz opened the month, August 4 to 9, and listed a ride midway. The Grahamsville Little World's Fair in Sullivan County took three days, August 14 to 16.
The Delaware County Fair in Walton followed August 17 to 22, and The Dutchess County Fair in Rhinebeck closed the month, August 25 to 30, though both dates were unconfirmed. The four fairs ran in four consecutive weeks without overlapping.
Rhinebeck, twice in one year
Rhinebeck has two events on the calendar, and so does Croton-on-Hudson. No other town in the region has more than one. The Dutchess County Fair was listed for August 25 to 30, a date that was not confirmed. The 2026 New York State Sheep & Wool Festival: October 15 to 18 at the same Dutchess County Fairgrounds, with sheep and fleece competitions and a vendor market for hand-spinners, knitters, and weavers.
Labor Day, then the harvest events
The Columbia County Fair in Chatham ran September 2 to 7, Labor Day week, on the same six days as the Fonda and Schaghticoke fairs.
Hudson Valley Garlic Festival ran September 26 to 27 at the Cantine Memorial Complex in Saugerties, Ulster County, organized by the Kiwanis Club of Saugerties. The Naples Grape Festival in the Finger Lakes ran the same two days.
Westchester: Hudson River Music Festival and the Blaze
Hudson River Music Festival was listed as the successor to Clearwater's Great Hudson River Revival, at Croton Point Park in Croton-on-Hudson, with a June 21 date that was unconfirmed.
The Great Jack O'Lantern Blaze is a hand-carved pumpkin installation staged by Historic Hudson Valley at Van Cortlandt Manor in the same town, on select evenings from September 18 to November 8, 2026. Entry: by timed ticket only, with advance tickets required.
