Three of these ten fairs overlapped on Labor Day weekend, and two shared October 2 to 4. Brooklyn and Chester come first in late August, and the Riverton Fair, October 9 to 11, comes last.
The ten are a selection. Hebron, Wapping and North Haven ran September 10 to 13, and Guilford, Orange, Four Town and Berlin fell between September 17 and 20.
Late August: Brooklyn and Chester
The Brooklyn Fair in Windham County was listed for August 27 to 30, though those 2026 dates were not confirmed. The Windham County Agricultural Society runs it. The fair was listed with ox draws, livestock shows and horse pulls, and adult admission at $12.
The Chester Fair ran August 28 to 30 on the Chester Fairgrounds in the lower Connecticut River Valley. The Chester Hose Company runs it. The program included a pie-baking contest and tractor pulls, and adult admission was $10.
Three fairs shared Labor Day weekend
The Woodstock Fair (September 3 to 7) had a demolition derby, a large commercial exhibit hall and headline entertainment, and adult admission was $15. The Haddam Neck Fair (September 4 to 7) had a horse and oxen draw, at $10 for adults. The Goshen Fair (September 5 to 7), on Route 63 in the Litchfield Hills, had woodsmen competitions and oxen and horse draws, with adult admission at $12.
All three ran through Monday, September 7.
Bethlehem, September 11 to 13
The Bethlehem Fair ran September 11 to 13 on the Bethlehem Fairgrounds, with 4-H shows and antique tractors. Adult admission was $12. None of the other nine fairs ran on those dates. Hebron, Wapping and North Haven, which are not among the ten, ran September 10 to 13 and overlapped it.
Durham, four days, September 24 to 27
The Durham Agricultural Fair Association has run the Durham Fair since 1916. In 2026 the fair ran September 24 to 27 on the Durham town green and surrounding fairgrounds, with a giant vegetable hall and grandstand concerts. Adult admission was $20 Friday through Sunday and $10 on Thursday. Children 11 and under were free.
Two fairs on October 2 to 4, then Riverton
The Harwinton Fair and the Portland Agricultural Fair both ran October 2 to 4. Harwinton had a woodsmen competition and antique tractors, and adult admission was $10. Portland, in the Connecticut River Valley, had tractor pulls. Adult admission there was $15 and on-site parking was $10.
The 2026 Riverton Fair: October 9 to 11 in the Litchfield Hills village of Riverton, with oxen draws and woodsmen events. Tickets $10 per person, fair parking free.
