The Dutchess County Fair returns Aug. 25 to 30 at the Dutchess County Fairgrounds. It’s an event that has run for over 180 years, and has become the premiere celebration of agriculture in the region.
The fair was first held in Pleasant Valley before moving to its current site on Route 9 in Rhinebeck. The fair has become one of the county’s largest annual events, and draws hundreds of thousands of visitors each year.
The 2026 program includes the fair’s mix of agricultural competitions, livestock judging, and horticultural exhibits, along with a one-room schoolhouse and an Antique Village Museum. The schoolhouse, which dates back to 1881, was originally located in Pine Plains. It was abandoned in the 1940s before being purchased and transported to the fairgrounds in 2004.
Other attractions include Livestock Hill — 12 acres dedicated to showcasing the finest in local livestock. It includes barns housing dairy cows, cattle, sheep, goats, poultry, rabbits, and more, along with milking demonstrations, a wool workroom, and sheep shearing.
Family activities include petting zoos with domestic and exotic animals, racing pigs, and dock diving dogs. The AgriVenture activity area includes a mock farm where children ages 3-10 can see how food is grown and sold. The kids can dig up potatoes from a sandbox, shear a wooden sheep, pick apples from a plywood tree, and milk “Dutchess” the cow.
Over 50 carnival rides will run throughout the fair. More than 100 food vendors are expected, and vendor rows will include artisans selling goods such as leather items, soaps, jewelry, and meat raised on local farms.
There’s also an emphasis on historical agriculture. A working sugar house, cider mill, and blacksmith shop are available to tour. Other artifacts include a turn-of-the-century printing press, firefighter’s museum, and a historic train station transported from Pleasant Valley.
The Grandstand lineup has musical acts lined up for the fair’s first five nights. Country star Chase Matthews will kick things off at 7:30 on August 25. He’ll be followed on subsequent nights by southern rockers 38 Special, Nashville’s Journey From the Heart, cover band Almost Queen, and troubadour Tyler Braden.
The last day’s festivities will trade music for cowpokes: the Painted Pony Championship Rodeo will take place at 11:30 a.m. and 5 p.m.
The fair’s annual livestock auction is scheduled for Saturday, August 29. The auction is organized in part through 4-H and FFA programs and draws farm families from across the county.
Gates open at 10 a.m. daily, and close at 10 p.m. Tuesday through Saturday. Sunday ends slightly earlier at 8 p.m.
Advance tickets are $15 for adults, or $18 at the gate. Admission is free for children under 11. Ride-all-day wristbands are $33 in advance and $40 at the gate. Parking is free, and a shuttle offers service from the Poughkeepsie MTA station.
