Enter below for your chance to win four (4) General Admission tickets and four (4) Unlimited Ride Wristbands to the 186th Annual Orange County Fair, returning to Middletown July 23 through August 2, 2026. New for 2026 at the Orange County FairThis year's fair introduces two incredible attractions making their Orange County Fair debut. Grandstand Action at the Orange County FairIf you love high-octane excitement, the Orange County Fair has plenty in store. No matter your age, there's something for everyone to enjoy at the Orange County Fair. The 186th Annual Orange County Fair runs July 23 through August 2, 2026.