There is nothing quite like a Connecticut fall fair — the smell of fried dough and barn animals, oxen straining against a stone boat, blue ribbons pinned to prize pumpkins, and a midway lighting up against the autumn dark. From the Litchfield Hills to the Quiet Corner, the state’s agricultural societies put on some of the oldest and best country fairs in New England.
This guide walks through the biggest and best fall fairs across Connecticut for 2026, organized roughly in the order they happen, so you can build out your September and October calendar.
The Big One: The Durham Fair
The Durham Fair (September 24–27, 2026) is Connecticut’s largest agricultural fair and the anchor of the state’s fall season. Held on the Durham town green and fairgrounds in the Connecticut River Valley since 1916, it draws crowds for its giant-vegetable hall, championship livestock, home-arts competitions, a sprawling midway, and grandstand concerts.
If you only make it to one Connecticut fair all year, this is the one. Arrive early — parking and crowds build quickly on Saturday.
Litchfield Hills Classics
Northwestern Connecticut is country-fair territory. The Goshen Fair (September 5–7, 2026) is a Labor Day weekend institution, famous for its woodsmen competitions and oxen draws. The Bethlehem Fair (September 11–13, 2026) follows the next weekend with livestock, antique tractors, and a busy midway.
The season winds down in the hills with the Harwinton Fair (October 2–4, 2026) and the traditional finale, the Riverton Fair (October 9–11, 2026), which keeps an old-time flavor in its scenic village setting.
The Quiet Corner & River Valley
In the northeast, the Woodstock Fair (September 3–7, 2026) is one of the state’s biggest, with a demolition derby, big-name entertainment, and a huge commercial hall over Labor Day weekend. Nearby, the Brooklyn Fair (August 27–30, 2026) bills itself as the oldest continuously operating agricultural fair in the country, dating to 1809.
Along the Connecticut River, the Chester Fair (August 28–30) and the Haddam Neck Fair (September 4–7) bring classic small-town fall fair charm, while the Portland Fair (October 2–4) rounds out the River Valley season.
Tips for Fair Season
Most Connecticut agricultural fairs charge $10–15 for adult admission, with children often free; some grange and 4-H fairs are free entirely. Admission usually covers parking and grounds access, while carnival rides and food are extra. Dress in layers — fall weather in Connecticut shifts fast — and bring some cash for the food booths.
Plan to spend at least a few hours to take in the livestock barns, a pulling competition, the exhibit halls, and a walk down the midway. That mix of agriculture, competition, and carnival is what makes a Connecticut fall fair feel timeless.
