Every fair on this list predates the automobile. Some predate the Civil War. Connecticut’s agricultural societies have been running county and town fairs continuously since the early 1800s, and a surprising number of the original organizations are still the ones putting on the show today, just with a midway and a demolition derby added somewhere along the way. This is a ranking of the state’s oldest fairs by the year they were founded, using each fair’s own stated founding year rather than a guess.
A note on what "oldest" means here: this ranks founding year, not necessarily unbroken annual operation, since a handful of these fairs paused during the World Wars or the 2020 pandemic before resuming. What they share is a real founding date well over a century old and a fair still running on it today.
1809: The Brooklyn Fair
The Brooklyn Fair is the oldest on this list by a wide margin, tracing back to 1809 in the Quiet Corner town of Brooklyn, and it’s regularly cited as one of the oldest continuously running agricultural fairs in the United States. Held every August, it keeps the format that defined fairs of this era: ox draws, livestock judging, and a country midway, the same basic shape a fairgoer in 1809 would recognize.
1838–1860: Four Town, Harwinton, Guilford, Goshen, and Woodstock
The next cluster of founding dates spans just over two decades. The Four Town Fair in Somers dates to 1838, serving the four surrounding towns since before Connecticut had a statewide rail network. The Harwinton Fair followed in 1853, and the Guilford Fair in 1859, giving the shoreline its own long-running agricultural tradition alongside the Litchfield Hills fairs. 1860 alone produced two: the Goshen Fair and the Woodstock Fair, both still anchoring their regions’ Labor Day weekend fair calendars a century and a half later.
1877–1916: Chester, Riverton, and Durham
The list closes out with three fairs founded between the late 1870s and the First World War. The Chester Fair began in 1877 in the River Valley and is known today for its 4-H shows and a pie contest that draws its own following. The Riverton Fair, founded in 1909, closes out the Litchfield Hills fair season every October in one of the region’s smaller villages. And the Durham Fair, founded in 1916, is the youngest fair on this particular list by founding year, yet it’s grown into the largest agricultural fair in the state, proof that founding date and current size don’t track together.
Why So Many Fairs Started in This Window
The concentration of founding dates in the 1800s isn’t a coincidence. Connecticut’s agricultural societies organized county and town fairs as a way to share farming knowledge and judge livestock and produce against a real standard, decades before extension services or 4-H existed to do the same job. Many of the organizing societies behind these fairs are still the legal entity running the event today, which is part of why a 19th-century fair can still feel like a genuine community institution rather than a revived novelty.
If you want to see fair history in person, pair one of these with a visit to a newer event on the same weekend; the contrast between a 200-year-old ox-draw tradition and a modern demolition derby, often on the very same fairgrounds, is part of what makes Connecticut’s fair season worth following county by county.
